ASYMMETRIC CYCLOPROPANATION OF 1-ALKENYLBORONIC ESTERS AND ITS APPLICATION TO THE SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPROPANOLS

被引：133

作者：

IMAI, T

MINETA, H

NISHIDA, S

机构：

[1] Department of Chemistry, Faculty of Science, Hokkaido University

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 17期

关键词：

D O I：

10.1021/jo00304a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric cyclopropanation of 1-alkenylboronic esters was realized by diastereofacial selective Simmons-Smith reaction of the esters modified by enantiomerically pure diols such as tetramethyltartar-amide. Subsequent oxidation of the resulting cyclo-propylboronates gave optically active 2-substituted cyclopropanols in 73-94% ee. These reactive compounds possess high synthetic potential. © 1990, American Chemical Society. All rights reserved.

引用

页码：4986 / 4988

页数：3

共 29 条

[1] AN ASYMMETRIC SIMMONS-SMITH REACTION
ARAI, I
MORI, A
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) : 8254 - 8256
[2] DEVELOPMENT OF A SIMPLE GENERAL PROCEDURE FOR SYNTHESIS OF PURE ENANTIOMERS VIA CHIRAL ORGANOBORANES
BROWN, HC
SINGARAM, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (08) : 287 - 293
[3] HYDROBORATION .55. HYDROBORATION OF ALKYNES WITH DIBROMOBORANE-DIMETHYL SULFIDE - CONVENIENT PREPARATION OF ALKENYLDIBROMOBORANES
BROWN, HC
CAMPBELL, JB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (03) : 389 - 395
[4] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE
BROWN, HC
GUPTA, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) : 5249 - 5255
[5] COLUMN DB, 1986, J AM CHEM SOC, V108, P2094
[6] CHEMISTRY OF CYCLOPROPANOLS .2. SYNTHETIC METHODS
DEPUY, CH
DAPPEN, GM
KLEIN, RA
EILERS, KL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) : 2813 - &
[7] CHEMISTRY OF CYCLOPROPANOLS
DEPUY, CH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1968, 1 (02) : 33 - &
[8] PALLADIUM-CATALYZED CONJUGATED DIENE SYNTHESIS FROM VINYLIC HALIDES AND OLEFINIC COMPOUNDS
DIECK, HA
HECK, RF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) : 1083 - 1090
[9] ASYMMETRIC SYNTHESIS VIA METALATED CHIRAL HYDRAZONES - ENANTIOSELECTIVE ALKYLATION OF CYCLIC-KETONES AND ALDEHYDES
ENDERS, D
EICHENAUER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (08): : 2933 - 2960
[10] A CONVENIENT HIGHLY STEREOSELECTIVE SYNTHESIS OF CYCLOPROPYLBORONATES
FONTANI, P
CARBONI, B
VAULTIER, M
CARRIE, R
[J]. TETRAHEDRON LETTERS, 1989, 30 (36) : 4815 - 4818

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