期刊
SYNLETT
卷 -, 期 3, 页码 345-348出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2003-37111
关键词
prins; skipped dienes; stereoelectronic; buttressing; cyclopropylmethyl cation
The reaction of 1-phenyldimethylsilyl-2-vinyl cyclopropane with aldehydes under the influence of dimethylaluminium chloride proceeds smoothly to provide skipped diene alcohols with exclusive E-olefin geometry regardless of the initial cis/trans configuration of the starting cyclopropane. The reaction is under stereoelectronic control where the Prins cation favours an anti-bisected conformation. A syn-bisected conformation can be partially induced by the introduction of a buttressing trimethylsilyl group on the cyclopropane ring, leading to competitive (masked) Z-skipped diene formation.
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