ENANTIOSELECTIVE CONSTRUCTION OF SPIRO(CYCLOPROPANE-1,4'-BICYCLO[3.3.0]OCT-1-EN-3-ONES)

被引：63
作者：
STOLLE, A
BECKER, H
SALAUN, J
DEMEIJERE, A
机构：
[1] UNIV PARIS 11,INST CHIM MOLEC ORSAY,CARBOCYCLES LAB,F-91405 ORSAY,FRANCE
[2] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 21期
关键词：
PAUSON-KHAND REACTION; INTRAMOLECULAR; METHYLENECYCLOPROPANES; DOUBLE BOND ACTIVATION IN; SPIRO(CYCLOPROPANE-1,4'-BICYCLO[3.3.0]OCT-1-EN-3-ONES) ENANTIOMERICALLY PURE COMPOUNDS; STEREOSELECTION;
D O I：
10.1016/S0040-4039(00)73225-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular Pauson-Khand reactions of 1,6-enynes 3a-c with a methylenecyclopropane terminator and a chiral acetal moiety adjacent to the triple bond gave spiro{cyclopropane-1,4'-bicyclo[3.3.0]oct-1-en-3-ones} 5a-c in good yields with a diastereoselectivity of up to 6.4:1. The major diastereomer of 5b was converted to enantiomerically pure bicyclo[3.3.0]octane-3,8-dione 8, which showed a negative peak at 287 nm in the CD curve, consistent with an assumed (5R) configuration.
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页码：3521 / 3524
页数：4
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