ASYMMETRIC VICINAL ACYLATION OF OLEFINS - A NEW APPROACH TO ENANTIOMERICALLY PURE GAMMA-LACTONES

被引：33

作者：

GENICOT, C ^{[1
]}

GHOSEZ, L ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN,CHIM ORGAN SYNTHESE LAB,PL LOUIS PASTEUR 1,B-1348 LOUVAIN,BELGIUM

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 48期

关键词：

KETENIMINIUM SALTS; 2+2] CYCLOADDITIONS; CYCLOBUTANONES; GAMMA-LACTONES; TRANS-2,5-DIMETHYLPYRROLIDINE;

D O I：

10.1016/S0040-4039(00)60187-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amide 3 derived from N-tosylsarcosine and (2R,5R)-dimethylpyrrolidine was converted into keteniminium salt 4 which readily cycloadded to olefins. Hydrolysis of the adducts yielded cyclobutanones which were regiospecifically oxidized to gamma-lactones 7. High enantioselectivities were observed with 1,2-cis-disubstitued olefins.

引用

页码：7357 / 7360

页数：4

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