Regio- and stereocontrolled hydrocyanation of chiral 2-alkylglycidamides with Et2AlCN:: synthesis of enantiomerically pure mono- and disubstituted malic acid derivatives

被引：0

作者：

Ruano, JLG ^{[1
]}

Fernández-Ibáñez, MA ^{[1
]}

Castro, AMM ^{[1
]}

Ramos, JHR ^{[1
]}

Flamarique, ACR ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ C1, E-28049 Madrid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 12期

关键词：

D O I：

暂无

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The opening of the oxirane ring of glycidamides with Et2AlCN takes place under mild conditions in a completely regio- and stereoselective manner to afford beta-cyano carboxamide derivatives, which are immediate precursors of mono- and disubstituted malic acid derivatives. The complete control of the regioselectivity can be rationalized as a consequence of the association of the reagent with the carboxamide group prior to intramolecular cyanide transfer. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1321 / 1325

页数：5

共 5 条

[1] REACTIONS OF CHIRAL BETA-KETOSULFOXIDES WITH ET2ALCN - ASYMMETRIC-SYNTHESIS OF CYANOHYDRIN DERIVATIVES
RUANO, JLG
CASTRO, AMM
RODRIGUEZ, JH
TETRAHEDRON LETTERS, 1991, 32 (27) : 3195 - 3198
[2] Regio- and diastereoselective synthesis of 5-trans-substituted and 5,5-disubstituted 2-pyrrolidinones derived from (S)-malic acid
Schuch, CM
Pilli, RA
TETRAHEDRON-ASYMMETRY, 2002, 13 (18) : 1973 - 1980
[3] First highly regio- and diastereoselective [3+2] cycloaddition of chiral nonracemic alkenyl Fischer carbene complexes with diazomethane derivatives:: Preparation and synthetic applications of enantiomerically pure Δ2-pyrazolines
Barluenga, J
Fernández-Marí, F
Viado, AL
Aguilar, E
Olano, B
García-Granda, S
Moya-Rubiera, C
CHEMISTRY-A EUROPEAN JOURNAL, 1999, 5 (03) : 883 - 896
[4] First highly regio- and diastereoselective [3+2] cycloaddition of chiral nonracemic alkenyl Fischer carbene complexes with diazomethane derivatives: Preparation and synthetic applications of enantiomerically pure Δ2-pyrazolines
Barluenga, Jose
Fernandez-Mari, Felix
Viado, Argimiro L.
Aguilar, Enrique
Olano, Bernardo
Garcia-Granda, Santiago
Moya-Rubiera, Carmen
Chemistry - A European Journal, 5 (03): : 883 - 896
[5] ASYMMETRIC-SYNTHESIS WITH CHIRAL 1,4-OXAZINE-2,5-DIONES - PREPARATION OF ENANTIOMERICALLY PURE 2-SUBSTITUTED PIPECOLIC ACID-DERIVATIVES
WANNER, KT
STAMENITIS, S
LIEBIGS ANNALEN DER CHEMIE, 1993, (05): : 477 - 484

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