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

页码：305 / 310

页数：6

共 28 条

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