AN ENANTIOSPECIFIC ENTRY TO FLUORO SUBSTITUTED AMINOCYCLOPENTANOLS THROUGH INTRAMOLECULAR NITRILE OXIDE, NITRONE, AND OXIME CYCLOADDITION REACTIONS

被引：26

作者：

ARNONE, A ^{[1
]}

CAVICCHIOLI, M ^{[1
]}

DONADELLI, A ^{[1
]}

RESNATI, G ^{[1
]}

机构：

[1] POLITECN MILAN,DIPARTIMENTO CHIM,CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20131 MILAN,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 06期

关键词：

D O I：

10.1016/0957-4166(94)80052-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Starting from (2R,3S)-2-benzyloxy-3-fluoro-5-hexenale 2 and its (2R,3R) epimer, cyclopentanoisoxazolidines 4 and 7 are obtained with complete diastereoselectivity through nitrone and oxime intramolecular cycloaddition reactions. In contrast, cyclopentanoisoxazolines 6 are formed with only medium stereoselectivity through intramolecular nitrile oxide cycloaddition reactions. Further elaboration of these bicyclic compounds affords fluoro substituted aminocyclopetanols 8 and 10 in enantiomerically and diastereoisomerically pure form.

引用

页码：1019 / 1028

页数：10

共 43 条

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