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On the stereochemistry of allylmetal‐aldehyde condensations . Preliminary communication
Author(s) -
Denmark Scott E.,
Weber Eric J.
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660604
Subject(s) - chemistry , aldehyde , intramolecular force , stereochemistry , fluoride , lewis acids and bases , condensation , catalysis , medicinal chemistry , organic chemistry , inorganic chemistry , physics , thermodynamics
The stereochemical course of the intramolecular allylsilane‐aldehyde condensation of 1a has been investigated. A modest preference for the product arising from a synclinal orientation of double bonds was observed with Lewis ‐acid catalysts. Cyclization induced by fluoride ion resulted in stereochemical reversal.