THE ENANTIOSELECTIVE FLUOROACETAMIDE ACETAL CLAISEN REARRANGEMENTS OF N-FLUOROACETYL-TRANS-(2R,5R)-2,5-DIMETHYLPYRROLIDINE

被引：36

作者：

YAMAZAKI, T

WELCH, JT

PLUMMER, JS

GIMI, RH

机构：

[1] Department of Chemistry, State University of New York at Albany, Albany

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 34期

关键词：

ENANTIOSELECTIVE AMIDE ACETAL CLAISEN REARRANGEMENT; N-FLUOROACETYL-TRANS-(2R,5R)-2,5-DIMETHYLPYRROLIDINE; ACETYL-TRANS-(2R,5R)-2,5-DIMETHYLPYRROLIDINE; DETERMINATION OF STEREOCHEMISTRY; METHYL TRIFLUOROMETHANESULFONATE;

D O I：

10.1016/S0040-4039(00)92145-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active monofluorinated amides were prepared via the amide acetal Claisen rearrangement and the establishment of the absolute stereochemistry of the rearranged products proved that the chiral auxiliary directed the approach of the crotyl fragment to the Si face of the (E)-N,O-ketene acetal. The general utility of this type of rearrangement is also discussed.

引用

页码：4267 / 4270

页数：4

共 30 条

[1]

ACS M, 1990, CHIMIA, V44, P90

[2] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS [J].