Diastereoselective synthesis of the nonracemic methyl syn-(3-fluoroalkyl)isoserinates

被引：78

作者：

Abouabdellah, A ^{[1
]}

Begue, JP ^{[1
]}

BonnetDelpon, D ^{[1
]}

Nga, TTT ^{[1
]}

机构：

[1] CNRS,URA 1843,CTR ETUD PHARMACEUT,F-92296 CHATENAY MALABR,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 25期

关键词：

D O I：

10.1021/jo971381a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (R-F = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%). However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.

引用

页码：8826 / 8833

页数：8

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