The evaluation of chiral benzosultams as auxiliaries in asymmetric azidation reaction

被引：41

作者：

Ahn, KH

Kim, SK

Ham, C

机构：

[1] POSTECH, Dept Chem, Pohang 790784, South Korea

[2] POSTECH, Ctr Biofunct Mol, Pohang 790784, South Korea

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 35期

关键词：

sultams; transfer hydrogenation; enantioselection; asymmetric reactions;

D O I：

10.1016/S0040-4039(98)01341-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several chiral 3-substituted benzosultams, synthesized through an enantioselective Ru(II)-catalyzed transfer hydrogenation of corresponding sulfonylimines. are evaluated as chiral auxiliaries in the asymmetric azidation reaction of their N-acyl derivatives. pi-Facial selectivities of up to 99:1 are observed. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6321 / 6322

页数：2

共 7 条

[1] Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides
Ahn, KH
Ham, C
Kim, SK
Cho, CW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) : 7047 - 7048
[2] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS
EVANS, DA
BRITTON, TC
ELLMAN, JA
DOROW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4011 - 4030
[3] ELECTROPHILIC AZIDE TRANSFER TO CHIRAL ENOLATES - A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS
EVANS, DA
BRITTON, TC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) : 6881 - 6883
[4] CHIRAL TOLUENE-2,ALPHA-SULTAM AUXILIARIES - ASYMMETRIC ALKYLATIONS, ACYLATIONS AND ALDOLIZATIONS OF N-ACYL DERIVATIVES
OPPOLZER, W
RODRIGUEZ, I
STARKEMANN, C
WALTHER, E
[J]. TETRAHEDRON LETTERS, 1990, 31 (35) : 5019 - 5022
[5] ENANTIOMERICALLY PURE ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL N-ACRYLOYL TOLUENE-2-ALPHA-SULTAMS
OPPOLZER, W
KINGMA, AJ
PILLAI, SK
[J]. TETRAHEDRON LETTERS, 1991, 32 (37) : 4893 - 4896
[6] CHIRAL TOLUENE-2,ALPHA-SULTAM AUXILIARIES - ASYMMETRIC DIELS-ALDER REACTIONS OF N-ENOYL DERIVATIVES
OPPOLZER, W
WILLS, M
KELLY, MJ
SIGNER, M
BLAGG, J
[J]. TETRAHEDRON LETTERS, 1990, 31 (35) : 5015 - 5018
[7] SEVDENPENNE J, 1995, CHIRAL AUXILIARIES L

← 1 →