CAMPHOR-DERIVED ALCOHOLS AS CHIRAL AUXILIARIES FOR ASYMMETRIC PAUSON-KHAND BICYCLIZATIONS - ENANTIOSELECTIVE SYNTHESIS OF ALPHA-METHOXYENONES

被引：51
作者：
VERDAGUER, X
MOYANO, A
PERICAS, MA
RIERA, A
GREENE, AE
PINIELLA, JF
ALVAREZLARENA, A
机构：
[1] UNIV BARCELONA,DEPT QUIM ORGAN,C MARTI & FRANQUES 1-11,E-08028 BARCELONA,SPAIN
[2] UNIV J FOURIER,LEDSS,F-38041 GRENOBLE,FRANCE
[3] UNIV AUTONOMA BARCELONA,DEPT GEOL,UNITAT CRISTALLOG,E-08193 BARCELONA,SPAIN
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1992年 / 433卷 / 03期
关键词：
D O I：
10.1016/0022-328X(92)80156-R
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The intramolecular Pauson-Khand reaction of enol and ynol ethers of Oppolzer's camphor-derived neopentyloxy alcohols is described. Bicyclic products are obtained in yields of up to 65% and with diastereoselectivities as high as 94:6 under very mild reaction conditions. The absolute configurations of the major stereoisomers obtained when (1R, 2S, 3R, 4S)-3-neopentyloxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol is used as a chiral auxiliary are rationalized on the basis of the theoretically predicted preferential conformations of model precursors. A simple procedure for obtaining auxiliary-free, enantiopure bicyclic alpha-methoxyenones is also presented.
引用
收藏
页码：305 / 310
页数：6
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