AMINO ACID-DERIVED CHIRAL ACYL NITROSO-COMPOUNDS - DIASTEREOSELECTIVITY IN INTERMOLECULAR HETERO-DIELS-ALDER REACTIONS

被引：82

作者：

RITTER, AR ^{[1
]}

MILLER, MJ ^{[1
]}

机构：

[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 16期

关键词：

D O I：

10.1021/jo00095a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

引用

页码：4602 / 4611

页数：10

共 27 条

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