SYNTHESIS OF HOMOCHIRAL AMINO-ALCOHOLS, AZIRIDINES AND DIAMINES VIA HOMOCHIRAL CYCLIC SULFITES

被引：97

作者：

LOHRAY, BB ^{[1
]}

AHUJA, JR ^{[1
]}

机构：

[1] NATL CHEM LAB,DIV ORGAN CHEM,POONA 411008,MAHARASHTRA,INDIA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 02期

关键词：

D O I：

10.1039/c39910000095

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Vicinal diols react with thionyl chloride to give 1,2-cyclic sulphites in quantitative yield, which undergo facile ring opening by lithium azide in dimethylformamide to yield azido alcohols and the latter in turn have been stereoselectively transformed into amino alcohols, aziridines and diamines.

引用

页码：95 / 97

页数：3

共 28 条

[1] A MILD, GENERAL PREPARATION OF N-ACYL AZIRIDINES AND 2-SUBSTITUTED 4(S)-BENZYLOXAZOLINES
BATES, GS
VARELAS, MA
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (23): : 2562 - 2566
[2] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS
COREY, EJ
YU, CM
LEE, DH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 878 - 879
[3] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM
COREY, EJ
IMWINKELRIED, R
PIKUL, S
XIANG, YB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5493 - 5495
[4] A PRACTICAL AND EFFICIENT METHOD FOR ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES
COREY, EJ
YU, CM
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5495 - 5496
[5] ENANTIOSELECTIVE VICINAL HYDROXYLATION OF TERMINAL AND E-1,2-DISUBSTITUTED OLEFINS BY A CHIRAL COMPLEX OF OSMIUM TETRAOXIDE - AN EFFECTIVE CONTROLLER SYSTEM AND A RATIONAL MECHANISTIC MODEL
COREY, EJ
JARDINE, PD
VIRGIL, S
YUEN, PW
CONNELL, RD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) : 9243 - 9244
[6] VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS
COREY, EJ
KIM, SS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) : 4976 - 4977
[7] EVANS DA, 1984, ASYMMETRIC SYNTHESIS, V3, P1
[8] VICINAL DIOL CYCLIC SULFATES - LIKE EPOXIDES ONLY MORE REACTIVE
GAO, Y
SHARPLESS, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7538 - 7539
[9] SUBSTITUTION OF OSIDIC CYCLIC SULFITES BY THE NITROGEN ION
GUILLER, A
GAGNIEU, CH
PACHECO, H
[J]. TETRAHEDRON LETTERS, 1985, 26 (51) : 6343 - 6344
[10] CIRCULAR-DICHROISM AND C-13 NUCLEAR MAGNETIC-RESONANCE STUDIES OF SOME PHENYL-SUBSTITUTED ETHYLENEDIAMINE-N,N,N',N'-TETRAACETATE ANALOGS
HAWN, GG
CHANG, CA
DOUGLAS, BE
[J]. INORGANIC CHEMISTRY, 1979, 18 (05) : 1266 - 1271

← 1 2 3 →