REGIOSELECTIVE CYCLOPROPANATION OF ALPHA-ALLENIC ALCOHOLS - AN EFFICIENT ROUTE TO ALKYLIDENECYCLOPROPANES

被引：51

作者：

LAUTENS, M

DELANGHE, PHM

机构：

[1] Department of Chemistry, University of Toronto, Toronto, Ontario

[2] Alfred P. Sloan Foundation, NSERC, University Research

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 19期

关键词：

D O I：

10.1021/jo00071a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly substituted alkylidenecyclopropanes are now easily accessible via a regioselective cyclopropanation of alpha-allenic alcohols using samarium/CH2I2. Dienols provide vinylcyclopropylcarbinols upon methylenation.

引用

页码：5037 / 5039

页数：3

共 50 条

[1] ASYMMETRIC TOTAL SYNTHESIS OF THE INDIVIDUAL DIASTEREOISOMERS OF HYPOGLYCIN-A [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BEBBINGTON, D ;

RUSSELL, AT .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (17) :1249-1251

[2] ALPHA-DEUTERIUM AND BETA-DEUTERIUM KINETIC ISOTOPE EFFECTS ON THE INACTIVATION OF THE GENERAL ACYL-COENZYME-A DEHYDROGENASE FROM PIG-KIDNEY BY (2-METHYLENECYCLOPROPANE)ACETYL-COA [J].

BALDWIN, JE ;

WIDDISON, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) :2245-2251

[3] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-)-ROTHROCKENE, A NON-HEAD-TO-TAIL MONOTERPENE [J].

BARBACHYN, MR ;

JOHNSON, CR ;

GLICK, MD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2746-2748

[4]

BERTRAND M, 1967, B SOC CHIM FR, P2779

[5]

BINGER P, 1987, TOP CURR CHEM, V135, P77

[6]

BRANDSMA L, 1981, SYNTHESIS ACETYLENES, P43

[7] ASYMMETRIC REDUCTION - REDUCTION OF ACETYLENIC KETONES WITH CHIRAL HYDRIDE AGENT [J].

BRINKMEYER, RS ;

KAPOOR, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) :8339-8341

[8] HIGHLY FUNCTIONALIZED VINYLCYCLOPROPANE DERIVATIVES BY REGIOSELECTIVE AND STEREOSELECTIVE REACTIONS OF FISCHER CARBENE COMPLEXES WITH 1,4-DISUBSTITUTED ELECTRON-DEFICIENT 1,3-DIENES [J].

BUCHERT, M ;

REISSIG, HU .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2723-2729

[9] A PRACTICAL AND GENERAL ENANTIOSELECTIVE SYNTHESIS OF CHIRAL PROPA-1,2-DIENYL AND PROPARGYL CARBINOLS [J].

COREY, EJ ;

YU, CM ;

LEE, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :878-879

[10] NEW STEREOSPECIFIC SYNTHETIC ROUTES TO TRISUBSTITUTED OLEFINS [J].

COREY, EJ ;

YAMAMOTO, H ;

HERRON, DK ;

ACHIWA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (22) :6635-&

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