Acyclic stereoselection. 22. Diastereofacial selectivity in the Lewis acid mediated reactions of allylsilanes with chiral aldehydes and enones

…, S Kiyooka, TA Blumenkopf

文献索引：Heathcock, Clayton H.; Kiyooka, Syun-ichi; Blumenkopf, Todd A. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4214 - 4223

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被引用次数: 111

摘要

The Lewis acid mediated reactions of chiral aldehydes 1-4 and enones 5-8 with allylsilanes 9 and 10 have been investigated. With aldehyde 1 and enones 5-7, modest diastereofacial preferences are seen, in the sense predicted by application of Felkin's model for asymmetric induction. Aldehydes 2-4 and enone 8 appear to react by way of chelated intermediates. With these four compounds, the diastereofacial preferences are rather large and are in the ...