Stereoselective reactions with imines

被引：27

作者：

Dai, LX ^{[1
]}

Lin, YR ^{[1
]}

Hou, XL ^{[1
]}

Zhou, YG ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China

来源：

PURE AND APPLIED CHEMISTRY | 1999年 / 71卷 / 06期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1351/pac199971061033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By the activation of general imines or using activated imines (N-tosylimines or N-diphenyl-phosphinoylimines), we developed three types of stereoselective reactions with imines: aldol reaction, allylation, and aziridiantion, and optically active 2-imidazolines and aziridines were obtained. According to experimental evidences, Sakurai-Hosomi reactions in the presence of catalytic amount of TBAF was demonstrated to be a fluoride-triggered autocatalytic mechanism. In addition, optically active 2,3-diamino acids were also synthesised conveniently by chemical transformations of 2-imidazolines.

引用

页码：1033 / 1040

页数：8

共 35 条

[1]

[Anonymous], [No title captured]

[2]

BENCHET P, 1992, TETRAHEDRON LETT, V33, P5959

[3] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[4] Lewis acid-catalyzed synthesis of aziridines [J].

Casarrubios, L ;

Perez, JA ;

Brookhart, M ;

Templeton, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359

[5] A SIMPLE, DIVERGENT, ASYMMETRIC-SYNTHESIS OF ALL MEMBERS OF THE 2,3,6-TRIDEOXY-3-AMINOHEXOSE FAMILY [J].

DAI, LX ;

LOU, BL ;

ZHANG, YZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) :5195-5196

[6] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[7] A MODIFICATION OF THE HIYAMA REACTION - SYNTHESIS OF HOMO ALLYLIC AMINES FROM IMINES AND ALLYLIC BROMIDES IN THE PRESENCE OF CRCL2 [J].

GIAMMARUCO, M ;

TADDEI, M ;

ULIVI, P .

TETRAHEDRON LETTERS, 1993, 34 (22) :3635-3638

[8] CHARACTERISTICS IN THE REACTIONS OF ALLYLSILANES AND THEIR APPLICATIONS TO VERSATILE SYNTHETIC EQUIVALENTS [J].

HOSOMI, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (05) :200-206

[9] Reaction of phosphinoyl-activated imines:: stereocontrolled synthesis of either trans- or cis-vinylaziridines [J].

Hou, XJ ;

Yang, XF ;

Dai, LX ;

Chen, XF .

CHEMICAL COMMUNICATIONS, 1998, (07) :747-748

[10] Addition of diethylzine to imines promoted by Lewis acid [J].

Hou, XL ;

Zheng, XL ;

Dai, LX .

TETRAHEDRON LETTERS, 1998, 39 (38) :6949-6952

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