OPTICALLY-ACTIVE CYCLOPROPANOLS BY SAMARIUM(II) IODIDE INDUCED INTRAMOLECULAR REDUCTIVE CYCLIZATION OF BETA-CHLOROSUBSTITUTED AMIDES

被引：13

作者：

FADEL, A

机构：

[1] Laboratoire des Carbocycles, Associé au CNRS, Institut de Chimie Moléculaire d'Orsay, 91405 Orsay Cedex

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 04期

关键词：

CHIRAL CYCLOPROPANOLS; BETA-CHLORO-ALKYL AMIDES; SAMARIUM IODIDE; INTRAMOLECULAR CYCLIZATION;

D O I：

10.1016/0957-4166(94)80010-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Samarium diiodide promotes under mild conditions, intramolecular reductive cyclisation of beta-chloro-substituted amides, and leads with an excellent diastereomeric excess and high yield to functionalised optically active cyclopropanols.

引用

页码：531 / 534

页数：4

共 17 条

[1] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

[2] A NEW AND CONVENIENT SYNTHESIS OF 1-AMINOCYCLOPROPANECARBOXYLIC ACID FROM CYCLOPROPANONE ACETAL [J].

FADEL, A .

TETRAHEDRON, 1991, 47 (32) :6265-6274

[3] OPTICALLY-ACTIVE ALPHA-ALKYLSUCCINATES FROM THE STEREOSELECTIVE ALKYLATION OF CHIRAL IMIDE ENOLATES [J].

FADEL, A ;

SALAUN, J .

TETRAHEDRON LETTERS, 1988, 29 (48) :6257-6260

[4]

FADEL A, 1990, SYNLETT, P89

[5]

FADEL A, 1993, SYNLETT, P503

[6]

FINN JM, 1989, Patent No. 434965

[7] RATE CONSTANTS FOR THE REACTIONS OF PRIMARY ALKYL RADICALS WITH SMI2 IN THF/HMPA [J].

HASEGAWA, E ;

CURRAN, DP .

TETRAHEDRON LETTERS, 1993, 34 (11) :1717-1720

[8]

KAGAN HB, 1990, NEW J CHEM, V14, P453

[9] ORGANIC-CHEMISTRY WITH LANTHANIDES [J].

KAGAN, HB ;

SASAKI, M ;

COLLIN, J .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1725-1730

[10] SEQUENTIAL RADICAL CYCLIZATION INTERMOLECULAR CARBONYL ADDITION-REACTIONS INITIATED BY SAMARIUM(II) IODIDE [J].

MOLANDER, GA ;

KENNY, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1439-1445

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