Academic literature on the topic 'Oppolzer's sultam'

Carsten Bolm of RWTH Aachen developed (Angew. Chem. Int. Ed. 2008, 47, 8920) an Ir catalyst that effected hydrogenation of trisubstituted enones such as 1 with high ee. Benjamin List of the Max-Planck-Institut Mülheim devised (J. Am. Chem. Soc. 2008, 130, 13862) an organocatalyst for the enantioselective reduction of nitro acrylates such as 3 with the Hantzsch ester 4. Gregory C. Fu of MIT optimized (J. Am. Chem. Soc. 2008, 130, 12645) a Ni catalyst for the enantioselective arylation of propargylic halides such as 6. Both enantiomers of 6 were converted to the single enantiomer of 8. Michael C. Willis of the University of Oxford established (J. Am. Chem. Soc. 2008, 130, 17232) that hydroacylation with a Rh catalyst was selective for one enantiomer of the allene 9, delivering 11 in high ee. Similarly, José Luis García Ruano of the Universidad Autónoma de Madrid found (Angew. Chem. Int. Ed. 2008, 47, 6836) that one enantiomer of racemic 13 reacted selectively with the enantiomerically- pure anion 12, to give 14 in high diastereomeric excess. Ei-chi Negishi of Purdue University described (Organic Lett. 2008, 10, 4311) the Zr-catalyzed asymmetric carboalumination (ZACA reaction) of the alkene 15 to give the useful chiron 16. David W. C. MacMillan of Princeton University developed (Science 2008, 322, 77) an intriguing visible light-powered oxidation-reduction approach to enantioselective aldehyde alkylation. The catalytic chiral secondary amine adds to the aldehyde to form an enamine, that then couples with the radical produced by reduction of the haloester. Two other alkylations were based on readily-available chiral auxiliaries. Philippe Karoyan of the Université Pierre et Marie Curie observed (Tetrahedron Lett . 2008, 49, 4704) that the acylated Oppolzer camphor sultam 20 condensed with the Mannich reagent 21 to give 22 as a single diastereomer. Andrew G. Myers of Harvard University developed the pseudoephedrine chiral auxiliary of 23 to direct the construction of ternary alkylated centers. He has now established (J. Am. Chem. Soc. 2008, 130, 13231) that further alkylation gave 24, having a quaternary alkylated center, in high diastereomeric excess.

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.