The evaluation of chiral benzosultams as auxiliaries in asymmetric azidation reaction

被引：42
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.
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页码：6321 / 6322
页数：2
相关论文
共 7 条
[1]   Practical synthesis of chiral sultam auxiliaries: 3-substituted-1,2-benzisothiazoline 1,1-dioxides [J].
Ahn, KH ;
Ham, C ;
Kim, SK ;
Cho, CW .
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 [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA ;
DOROW, RL .
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 [J].
EVANS, DA ;
BRITTON, TC .
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 [J].
OPPOLZER, W ;
RODRIGUEZ, I ;
STARKEMANN, C ;
WALTHER, E .
TETRAHEDRON LETTERS, 1990, 31 (35) :5019-5022
[5]   ENANTIOMERICALLY PURE ISOXAZOLINES VIA ADDITION OF NITRILE OXIDES TO CHIRAL N-ACRYLOYL TOLUENE-2-ALPHA-SULTAMS [J].
OPPOLZER, W ;
KINGMA, AJ ;
PILLAI, SK .
TETRAHEDRON LETTERS, 1991, 32 (37) :4893-4896
[6]   CHIRAL TOLUENE-2,ALPHA-SULTAM AUXILIARIES - ASYMMETRIC DIELS-ALDER REACTIONS OF N-ENOYL DERIVATIVES [J].
OPPOLZER, W ;
WILLS, M ;
KELLY, MJ ;
SIGNER, M ;
BLAGG, J .
TETRAHEDRON LETTERS, 1990, 31 (35) :5015-5018
[7]  
SEVDENPENNE J, 1995, CHIRAL AUXILIARIES L
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