Academic literature on the topic 'Pyrrolidinone derive'

Ryoichi Kuwano of Kyushu University showed (J. Am. Chem. Soc. 2008, 130, 808) that diastereomerically and enantiomerically pure pyrollidines such as 2 could be prepared by hydrogenation of the corresponding pyrrole. Victor S. Martín of Universidad de la Laguna found (Organic Lett. 2008, 10, 2349) that the stereochemical outcome of the pyrrolidine-forming Nicholas cyclization could be directed by the protecting group on the N. Jianbo Wang of Peking University established (J. Org. Chem. 2008, 73, 1971) a convenient route to diazo esters such as 6. N-H insertion led to the pyrrolidine, which Zhen-Jiang Xu of the Shanghai Institute of Organic Chemistry and Chi-Ming Che of the University of Hong Kong showed (Organic Lett. 2008, 10, 1529) could be reduced with high diastereoselectivity to the hydroxy ester 7. Alternatively, Professor Wang found that photochemical Wolff rearrangement of 6 delivered the pyrrolidone 8 . Martin J. Slater and Shiping Xie of GlaxoSmithKline optimized (J. Org. Chem. 2008, 73, 3094) the hydroquinine catalyzed enantioselective 3+2 cycloaddition of 9 and 10, leading to the pyrrolidine 11 with high diastereocontrol. Shu Kobayashi of the University of Tokyo developed (Adv. Synth. Cat. 2008, 350, 647) a practical protocol for the aza Diels-Alder construction of enantiomerically-pure piperidines such as 14 . Biao Yu of the Shanghai Institute of Organic Chemistry cyclized (Tetrahedron Lett. 2008, 49, 672) the product from the proline-catalyzed enantioselective aldol of 15 and 16, leading to the substituted piperidine 17 . Michael Shipman of the University of Warwick described (Tetrahedron Lett. 2008, 49, 250) the cyclization of the aziridine derived from 18, that proceeded to give 19 as a single diastereomer, apparently via kinetic side-chain protonation. Takeo Kawabata of Kyoto University found (J. Am. Chem. Soc. 2008, 130, 4153) that intramolecular alkylation to form four, five and six-membered rings from amino esters such as 21 proceeded with remarkable enantioretention. Géraldine Masson and Jieping Zhu of CNRS, Gif-sur-Yvette, condensed (Organic Lett. 2008, 10, 1509) cinnamaldehyde 23 with cyanide and an ω-alkenyl amine to give the intramolecular aza-Diels-Alder substrate 24. Hongbin Zhai of the Shanghai Institute of Organic Chemistry acylated (J. Org. Chem. 2008, 73, 3589) 26 with 27, leading to the ring-closing metathesis precursor 28.

Keiji Maruoka of Kyoto University found (Organic Lett. 2010, 12, 1668) that the diazo amide 1 derived from the Oppolzer sultam condensed with the imine 2 to give the aziridine 3 with high stereocontrol. Andrei K. Yudin of the University of Toronto observed (Angew. Chem. Int. Ed. 2010, 49, 1607) that the unprotected aziridine aldehyde 4, which exists as a mixture of dimers, condensed smoothly with the Ohira reagent 5 to give the alkynyl aziridine 6. David M. Hodgson of the University of Oxford successfully (Angew. Chem. Int. Ed. 2010, 49, 2900) deprotonated the azetidine thioamide 7 to give, after allylation, the azetidine 8. Varinder K. Aggarwal of the University of Bristol devised (Chem. Commun. 2010, 267) a Pd catalyst for the cyclocarbonylation of an alkenyl aziridine 9 to give the β-lactam 10. Iain Coldham of the University of Sheffield used (J. Org. Chem. 2010, 75, 4069) the ligand they had developed to effect enantioselective allylation of the pyrrolidine derivative 11. The corrresponding piperidine worked as well. John P. Wolfe of the University of Michigan established (Organic Lett. 2010, 12, 2322) that the Pd-mediated cyclization of 13 to 15 could be effected with high diastereocontrol. Christopher G. Frost of the University of Bath optimized (Angew. Chem. Int. Ed. 2010, 49, 1825) the tandem Ru-mediated conjugate addition/cyclization of 16 to give 18 in high ee. Barry M. Trost of Stanford University extended (J. Am. Chem. Soc. 2010, 132, 8238) their studies of trimethylenemethane cycloaddition to the ketimine 19, leading to the substituted pyrrolidine 21 in high ee. Pher G. Andersson of Uppsala University optimized (J. Am. Chem. Soc. 2010, 132, 8880) an Ir catalyst for the enantioselective hydrogenation of readily prepared tetrahydropyridines such as 22. Min Shi of the Shanghai Institute of Organic Chemistry devised (J. Org. Chem. 2010, 75, 3935) a Pd catalyst for enantioselective conjugate addition to the prochiral pyridone 24. Xiaojun Huang of Roche Palo Alto prepared (Tetrahedron Lett. 2010, 51, 1554) the monoacid 26 by enantioselective methanolysis of the anhydride. Selective formylation of the ester led to the pyridone 27.

Magnus Rueping of RWTH Aachen University found (Chem. Commun. 2015, 51, 2111) that under Fe catalysis, a Grignard reagent would couple with the iodoazetidine 1 to give the substituted azetidine 2. Timothy F. Jamison of MIT established (Chem. Eur. J. 2015, 21, 7379) a protocol for converting 3, readily available from commercial homoserine lactone, to the alkylated azetidine 4. Long-Wu Ye of Xiamen University used (Chem. Commun. 2015, 51, 2126) a gold catalyst to cyclize 5, readily prepared in high ee, to the versatile ene sulfonamide 6. Chang- Hua Ding and Xue-Long Hou of the Shanghai Institute of Organic Chemistry added (Angew. Chem. Int. Ed. 2015, 54, 1604) the racemic aziridine 7 to the enone 8 to give the pyrrolidine 9 in high ee. Arumugam Sudalai of the National Chemical Laboratory employed (J. Org. Chem. 2015, 80, 2024) proline as an organocatalyst to mediate the addition of 11 to 10, leading to the pyrrolidine 12. Aaron D. Sadow of Iowa State University developed (J. Am. Chem. Soc. 2015, 137, 425) a Zr catalyst for the enantioselective cyclization of the prochiral 13 to 14. Masahiro Murakami of Kyoto University devised (Angew. Chem. Int. Ed. 2015, 54, 7418) a Rh catalyst for the enantioselective ring expansion of the photocycliza­tion product of 15 to the enamine 16. Sebastian Stecko and Bartlomiej Furman of the Polish Academy of Sciences reduced (J. Org. Chem. 2015, 80, 3621) the carbohydrate-derived lactam 17 with the Schwartz reagent to give an intermediate that could be coupled with an isonitrile, leading to the amide 18. Lei Liu of Shandong University oxidized (Angew. Chem. Int. Ed. 2015, 54, 6012) the alkene 19 in the presence of 20 to give 21. Tomislav Rovis of Colorado State University optimized (J. Am. Chem. Soc. 2015, 137, 4445) a Zn catalyst for the addition of 22 to the nitro alkene 23, leading, after reduction, to the piperidine 24. Carlos del Pozo and Santos Fustero of the Universidad de Valencia used (Org. Lett. 2015, 17, 960) a chiral auxiliary to direct the cyclization of 25 to the bicyclic amine 26. In another illustration of the use of microwave irradiation to activate amide bond rotation, G. Maayan of Technion showed (Org. Lett. 2015, 17, 2110) that 27 could be cyclized efficiently to the medium ring lactam 28.

Forrest E. Michael of the University of Washington described (Organic Lett. 2009, 11, 1147) the Pd-catalyzed aminative cyclization of 1 to the differentially-protected diamine 3. Peter Somfai of KTH Chemical Science and Engineering observed (Organic Lett. 2009, 11, 919) that [1,2]-rearrangement of 4 proceeded to deliver 5 with near-perfect maintenance of enantiomeric excess. Tushar Kanti Chakraborty of the Central Drug Research Institute, Lucknow applied (Tetrahedron Lett. 2009, 50, 3306) the Ti(III) reduction of epoxides to the Sharpless-derived ether 6, leading to the pyrrolidine 7. Chun-Jiang Wang of Wuhan University devised (Chem. Commun. 2009, 2905) a silver catalyst that directed the absolute sense of the dipolar addition of 9 to 8 to give 10. Homoallyic azides such as 11 are readily prepared in high enantiomeric excess from the corresponding alcohol. Bernhard Breit of Albert-Ludwigs-Universität, Freiburg and André Mann of the Faculté de Pharmacie, Illkirch showed (Organic Lett. 2009, 11, 261) that Rh-mediated hydroformylation could be effected in the presence of the azide. Subsequent reduction delivered the piperidine 12. Jan-E. Bäckvall of Stockholm University applied (J. Org. Chem. 2009, 74, 1988) the protocol for dynamic kinetic asymmetric transformation (DYKAT) that he had developed to the cyanodiol 13. Remarkably, a single enantiomerically- pure diasteromer emerged, which he carried on to 14. Xiaodong Shi of West Virginia University found (Organic Lett. 2009, 11, 2333) that the stereogenic center of 17, even though it ended up outside the ring, directed the absolute configuration of the other centers of 18 as they formed. Jan Vesely of Charles University and Albert Moyano and Ramon Rios of the Universitat de Barcelona established (Tetrahedron Lett. 2009, 50, 1943) that an organocatayst directed the absolute configuration in the addition of 19 to 20 to give 21. Osamu Tamura of Showa Pharmaceutical University effected (Organic Lett. 2009, 11, 1179) cyclization of the malic acid-derived amide 22 to give 23 with high diastereocontrol.

Terminal epoxides such as 1 are readily available in high enantiomeric excess. Christopher D. Bray of Queen Mary University of London observed (Tetrahedron Lett. 2014, 55, 5890) clean inversion in the conversion of 1 to the aziridine 3 with the reagent 2. Yong-Chun Luo and Peng-Fei Xu of Lanzhou University opened (Org. Lett. 2014, 16, 4896) the activated cyclopropane 4 with benzyl azide, then heated the adduct to expel N2, leading to the azetidine 5. Zhenming Du of Roche Shanghai and Michelangelo Scalone of Roche Basel devel­oped (Org. Process Res. Dev. 2014, 18, 1702) practical conditions for the asymmetric hydrogenation of 6 to the pyrrolidine 7. Young Ho Rhee of the Pohang University of Science and Technology showed (Chem. Eur. J. 2014, 20, 16391) that depending on the diol protecting group, addition of allyl silane to 8 could lead to either the cis product 9 or the trans diastereomer (not illustrated). Ohyun Kwon of UCLA used (J. Am. Chem. Soc. 2014, 136, 11890) an organocatalyst to add the racemic allene 10 to 11 to give 12 in high ee. Tom Livinghouse of Montana State University cyclized (Angew. Chem. Int. Ed. 2014, 53, 14352) the hydrazine 13 into an intermediate organozinc species that was then coupled with allyl bromide to give 14. Yonggang Chen of Merck Process and Xumu Zhang of Rutgers University devised (Angew. Chem. Int. Ed. 2014, 53, 12761) practical conditions for the reduction of 15 to the piperidine 16. Teck-Peng Loh of the Nanyang Technological University and the University of Science and Technology of China effected (Chem. Commun. 2014, 50, 8324) asymmetric phenylation of biomass-derived 17 to give an intermediate that was oxidatively rearranged, then reduced to 18. Robert R. Knowles of Princeton University showed (J. Am. Chem. Soc. 2014, 136, 12217) that the cyclization of 19 to 20 proceeded with high diastereoselectivity. Maria J. Alves of the Universidade do Minho osmylated (Synlett 2014, 25, 1751) the adduct from the Diels–Alder cycload­dition of 22 to 21 to give 23 in high ee.

Konstantin P. Bryliakov of the Boreskov Institute of Catalysis devised (Org. Lett. 2012, 14, 4310) a manganese catalyst for the selective tertiary hydroxylation of 1 to give 2. Note that the electron-withdrawing Br deactivates the alternative methine H. Bhisma K. Patel of the Indian Institute of Technology, Guwahati selectively oxidized (Org. Lett. 2012, 14, 3982) a benzylic C–H of 3 to give the corresponding benzoate 4. Dalibor Sames of Columbia University cyclized (J. Org. Chem. 2012, 77, 6689) 5 to 6 by intramolecular hydride abstraction followed by recombination. Thomas Lectka of Johns Hopkins University showed (Angew. Chem. Int. Ed. 2012, 51, 10580) that direct C–H fluorination of 7 occurred predominantly at carbons 3 and 5. John T. Groves of Princeton University reported (Science 2012, 337, 1322) an alternative manganese porphyrin catalyst (not illustrated) for direct fluorination. C–H functionalization can also be mediated by a proximal functional group. John F. Hartwig of the University of California, Berkeley effected (J. Am. Chem. Soc. 2012, 134, 12422) Ir-mediated borylation of an ether 9 in the position β to the oxygen to give 10. Uttam K. Tambar of the UT Southwestern Medical Center devised (J. Am. Chem. Soc. 2012, 134, 18495) a protocol for the net enantioselective amination of 11 to give 12. Conversion of a C–H bond to a C–C bond can be carried out in an intramolecular or an intermolecular sense. Kilian Muñiz of the Catalan Institution for Research and Advanced Studies cyclized (J. Am. Chem. Soc. 2012, 134, 15505) the terminal alkene 13 directly to the cyclopentene 15. Olivier Baudoin of Université Claude Bernard Lyon 1 closed (Angew. Chem. Int. Ed. 2012, 51, 10399) the pyrrolidine ring of 17 by selective activation of a methyl C–H of 16. Jeremy A. May of the University of Houston found (J. Am. Chem. Soc. 2012, 134, 17877) that the Rh carbene derived from 18 inserted into the distal alkyne to give a new Rh carbene 19, which in turn inserted into a C–H bond adjacent to the ether oxygen to give 20.