ENZYME-CATALYZED REACTIONS .11. SYNTHESIS AND STEREOSELECTIVE REACTIONS OF (R)-ALPHA-SULFONYLOXYNITRILES

被引：72

作者：

EFFENBERGER, F ^{[1
]}

STELZER, U ^{[1
]}

机构：

[1] UNIV STUTTGART,INST ORGAN CHEM,PFAFFENWALDRING 55,W-7000 STUTTGART 80,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 07期

关键词：

D O I：

10.1002/anie.199108731

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The sulfonylation of (R)-cyanohydrins (R)-1 to form (R)-2 takes place without racemization. The conversion-also without racemization but with inversion-of (R)-2 by nucleophiles (Nu = OAc, N3, N-phthaloyl) yields cyanohydrins (S)-3, which are interesting as synthetic intermediates.

引用

页码：873 / 874

页数：2

共 26 条

[1] STEREOSPECIFIC SYNTHESIS OF D-HYDROXYNITRILES AND OPTICALLY ACTIVE ETHANOLAMINES [J].

BECKER, W ;

FREUND, H ;

PFEIL, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1965, 4 (12) :1079-&

[2]

BECKER W, 1965, ANGEW CHEM, V77, P1139

[3]

BRUNNER H, 1985, EUR J MED CHEM, V20, P509

[4] SUBSTITUTION OF 2-(SULFONYLOXY)CARBOXYLATES WITH OXYGENE AND SULFUR NUCLEOPHILES WITHOUT RACEMIZATION [J].

BURKARD, U ;

EFFENBERGER, F .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (05) :1594-1612

[5] AZIRIDINES [J].

DEYRUP, JA .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS-A SERIES OF MONOGRAPHS, 1983, 42 :1-214

[6] ALPHA-CYANOALKYL SULFONATES .1. THE REACTIONS OF ALPHA-CYANOBENZYL BENZENESULFONATE [J].

DODSON, RM ;

TURNER, HW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (10) :4517-4519

[7] ENZYME-CATALYZED CYANOHYDRIN SYNTHESIS IN ORGANIC-SOLVENTS [J].

EFFENBERGER, F ;

ZIEGLER, T ;

FORSTER, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (05) :458-460

[8]

EFFENBERGER F, 1991, LIEBIGS ANN CHEM, P47

[9]

EFFENBERGER F, 1986, LIEBIGS ANN CHEM, P314

[10] ENZYME-CATALYZED REACTIONS .5. ENZYME-CATALYZED SYNTHESIS OF (S)-CYANOHYDRINS AND SUBSEQUENT HYDROLYSIS TO (S)-ALPHA-HYDROXY-CARBOXYLIC ACIDS [J].

EFFENBERGER, F ;

HORSCH, B ;

FORSTER, S ;

ZIEGLER, T .

TETRAHEDRON LETTERS, 1990, 31 (09) :1249-1252

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