Academic literature on the topic 'Hydrolysis of alkyl ether sulfates'

Bekington Myrboh of North-Eastern Hill University reported (Tetrahedron Lett. 2010, 51, 2862) a convenient procedure for the oxidative removal of a 1,3-oxathiolane 1 or a 1,3-dithiolane. Sang-Gyeong Lee and Yong-Jin Yoon of Gyeongsang National University developed (J. Org. Chem. 2010, 75, 484) the pyridazin-3(2H )-one 4 for the microwave-mediated deprotection of an oxime 3. Dario M. Bassani of Université Bordeaux 1 and John S. Snaith of the University of Birmingham devised (J. Org. Chem. 2010, 75, 4648) a procedure for the facile preparation of esters such as 6. Brief photolysis (350 nm) returned the parent carboxylic acid 7. Craig M. Williams of the University of Queensland prepared (Tetrahedron Lett. 2010, 51, 1158) the trithioorthoester 8 by iterative opening of epichlorohydrin. He found that the keto ester 9 could be efficiently released by Hg-mediated hydrolysis. Masatoshi Mihara of the Osaka Municipal Technical Research Institute established (Synlett 2010, 253) that even very congested alcohols such as 10 could be acetylated by acetic anhydride containing a trace of FeCl3. Colleen N. Scott, now at Southern Illinois University, developed (J. Org. Chem. 2010, 75, 253) a convenient procedure for the preparation of the hydridosilane 13, which on Mn catalysis added the alcohol 12 to make the unsymmetrical bisalkoxysilane 14. Sabine Berteina-Raboin of the Université d’Orléans found (Tetrahedron Lett. 2010, 51, 2115) that NaBH4 in EtOH cleanly removed the chloroacetates from 15. Both other esters and silyl ethers were stable under these conditions. Ram S. Mohan of Illinois Wesleyan University established (Tetrahedron Lett. 2010, 51, 1056) that Fe(III) tosylate in methanol selectively removed the alkyl silyl ether from 17 without affecting the aryl silyl ether. Alakananda Hajra and Adinath Majee of Visva-Bharati University effected (Tetrahedron Lett. 2010, 51, 2896) formylation of an amine 19 by heating with commercial 85% formic acid as the solvent in a sealed tube at 80°C. Although both primary and secondary amines could be effi ciently formylated, the primary amines were much more reactive. Doo Ok Jang of Yonsei University found (Tetrahedron Lett. 2010, 51, 683) that the conveniently handled CF3CCO2H (the acid chloride is a gas) could be activated in situ to selectively convert 22 into 24.

Yuqing Hou of Southern Illinois University found (J. Org. Chem. 2009, 74, 6362) that the peroxy ether 2 served effectively to directly transfer a methoxy group to the lithiated 1 to give 3. Wanzhi Chen of Zhejiang University, Xixi Campus, showed (J. Org. Chem. 2009, 74, 7203) that pyrimidines such as 4, readily prepared from the corresponding phenol, underwent smooth Pd-catalyzed ortho acetoxylation. Trond Vidar Hansen of the University of Oslo observed (Tetrahedron Lett. 2009, 50, 6339) that simple electrophilic formylation of phenols such as 6 also proceeded with high ortho selectivity. Kyung Woon Jung of the University of Southern California optimized (J. Org. Chem. 2009, 74, 6231) the Rh catalyst for ortho C-H insertion, converting 8 into 9. Jin-Quan Yu of Scripps/La Jolla devised (Science 2010, 327, 315) a protocol for carboxy-directed catalytic ortho palladation that allowed subsequent Heck coupling, transforming 10 into 11. Norikazu Miyoshi of the University of Tokushima established (Chem. Lett. 2009, 38, 996) that in situ generated strontium alkyls added 1,6 to benzoic acid 13, to give, after mild oxidative workup, the 4-alkyl benzoic acid 15. Amin Zarei of Islamic Azad University showed (Tetrahedron Lett. 2009, 50, 4443) that their previously developed protocol for preparing stable diazonium silica sulfates could be extended to the preparation of an aryl azide such as 17. Stephen L. Buchwald of MIT developed (J. Am. Chem. Soc. 2009, 131, 12898) a Pd-mediated protocol for the conversion of aryl chlorides to the corresponding nitro aromatics. Virgil Percec of the University of Pennsylvania has also reported (Organic Lett. 2009, 11, 4974) the conversion of an aryl chloride to the borane, and Guy C. Lloyd-Jones has described (Angew. Chem. Int. Ed. 2009, 48, 7612) the conversion of phenols to the corresponding thiols. Kwang Ho Song of Korea University and Sunwoo Lee of Chonnam National University demonstrated (J. Org. Chem. 2009, 74, 6358) that the Ni-mediated homologation of aryl halides worked with a variety of primary and secondary formamides. Kwangyong Park of Chung-Ang University observed (J. Org. Chem. 2009, 74, 9566) that Ni catalysts also mediated the coupling of Grignard reagents with the tosylate 22 not in the usual way but with the C-S bond to give 23.

Enzymatic reduction of a ketone can proceed in high enantiomeric excess, but this would require a stoichiometric amount of a reducing agent. Wolfgang Kroutil of the Karl-Franzens-Universität Graz devised (Angew. Chem. Int. Ed. 2008, 47, 741) a protocol for preparing the alcohol 2 in high ee starting from the racemic alcohol. The alcohol dehydrogenase chosen was selective for the R-alcohol, and the microorganism reduced the ketone so produced selectively to the S alcohol. James M. Takacs of the University of Nebraska established (J. Am. Chem. Soc. 2008, 130, 3734) that chiral Rh catalyzed addition of pinacolborane to a β,γ-unsaturated N-phenyl amide 3 proceeded with high enantiocontrol. The product organoborane was oxidized to the alcohol 4 . J. R. Falck of the UT Southwestern Medical Center used (J. Am. Chem. Soc. 2008, 130, 46) an organocatalyst to effect addition of phenylboronic acid to the γ-hydroxy enone 5, to give, after hydrolysis, the diol 6. John F. Hartwig of the University of Illinois effectively telescoped (Angew. Chem. Int. Ed. 2008, 47, 1928) alcohol formation and protection into a single step, by developing a procedure for the direct conversion of a primary allylic acetate 7 to the enantiomerically-enriched secondary benzyl ether 8. Tsutomu Katsuki of Kyushu University designed (Chemistry Lett. 2008, 37, 502) a catalyst for the enantioselective hydrocyanation of an aldehyde 9, by HCN transfer from the inexpensive 10. Mei-Xiang Wang of the Chinese Academy of Sciences, Beijing and Jieping Zhu of CNRS, Gif-sur-Yvette devised (Angew. Chem. Int. Ed. 2008, 47, 388) a catalyst for a complementary one-carbon homologation, the enantioselective Passerini three-component coupling of an aldehyde 12, an isonitrile 13, and an acid 14. Joseph M. Ready, also of UT Southwestern, developed (J. Am. Chem. Soc. 2008, 130, 7828) the preparation of enol benzoates such as 17 from the corresponding alkynes. Sharpless asymmetric dihydroxylation of 17 proceeded with high ee to give, after reduction, the diol 18. Toshiro Harada of the Kyoto Institute of Technology described (Angew. Chem. Int. Ed. 2008, 47, 1088) a potentially very practical enantioselective homologation, the catalyzed addition of an alkyl titanium, prepared in situ from the corresponding Grignard reagent, to the aldehyde 19, to give 21 in high ee.