DIASTEREOSELECTIVITY AND REGIOCONTROL IN INTRAMOLECULAR ALLYL CATION CYCLOADDITIONS - SELECTIVE FORMATION OF [3+2] OR [3+4] CYCLOADDUCTS

被引:36
作者
GIGUERE, RJ [1 ]
TASSELY, SM [1 ]
ROSE, MI [1 ]
KRISHNAMURTHY, VV [1 ]
机构
[1] VARIAN ASSOCIATES INC,DIV NUCL MAGNET RESONANCE INSTRUMENTS,FLORHAM PK,NJ 07932
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)97680-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular Hoffmann-Noyori reactions of chiral, diastereomeric trienols 1a and 1b demonstrate site-selectivity control to form either [3+4] or [3+2] cycloadducts 2a and 2b, respectively. Furthermore, both reactions exhibit a high degree of diastereoselectivity. Cycloaddition precursors 1a,b are prepared from (-)-S-citronellol in 33% overall yield. © 1990.
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页码:4577 / 4580
页数:4
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