ENANTIOSELECTIVE CONVERSION OF ALDEHYDES TO CYANOHYDRINS BY A CATALYTIC-SYSTEM WITH SEPARATE CHIRAL BINDING-SITES FOR ALDEHYDE AND CYANIDE COMPONENTS

被引：144

作者：

COREY, EJ

WANG, Z

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)60600-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new enantioselective method for the synthesis of chiral cyanohydrins from aldehydes and trimethylsilyl cyanide is described which uses a pair of synergistic chiral reagents, one to activate the aldehyde and the other to provide an equivalent of chiral cyanide ion.

引用

页码：4001 / 4004

页数：4

共 17 条

[1] O-SULFINYLATION WITH METHANESULFONYL CYANIDE OR PARA-TOLUENESULFONYL CYANIDE AND DBU+
BARTON, DHR
JASZBERENYI, JC
THEODORAKIS, EA
[J]. TETRAHEDRON LETTERS, 1991, 32 (23) : 2585 - 2588
[2] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX
COREY, EJ
IMAI, N
ZHANG, HY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 728 - 729
[3] HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX
COREY, EJ
ISHIHARA, K
[J]. TETRAHEDRON LETTERS, 1992, 33 (45) : 6807 - 6810
[4] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
EVANS, DA
WOERPEL, KA
HINMAN, MM
FAUL, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
[5] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES CATALYZED BY CHIRAL SCHIFF-BASE TITANIUM ALKOXIDE COMPLEXES
HAYASHI, M
MIYAMOTO, Y
INOUE, T
OGUNI, N
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1515 - 1522
[6] ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES PROMOTED BY MODIFIED SHARPLESS CATALYST
HAYASHI, M
MATSUDA, T
OGUNI, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (19) : 1364 - 1365
[7] LIPASE-CATALYZED KINETIC RESOLUTION WITH INSITU RACEMIZATION - ONE-POT SYNTHESIS OF OPTICALLY-ACTIVE CYANOHYDRIN ACETATES FROM ALDEHYDES
INAGAKI, M
HIRATAKE, J
NISHIOKA, T
ODA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9360 - 9361
[8] ENANTIOSELECTIVE ADDITION-REACTION OF TRIMETHYLSILYL CYANIDE WITH ALDEHYDES USING A CHIRAL TIN(II) LEWIS ACID
KOBAYASHI, S
TSUCHIYA, Y
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1991, (04) : 541 - 544
[9] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES
LOWENTHAL, RE
ABIKO, A
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6005 - 6008
[10] ASYMMETRIC COPPER-CATALYZED CYCLOPROPANATION OF TRISUBSTITUTED AND UNSYMMETRICAL CIS-1,2-DISUBSTITUTED OLEFINS - MODIFIED BIS-OXAZOLINE LIGANDS
LOWENTHAL, RE
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (50) : 7373 - 7376

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