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Synthesis and Intramolecular Aldol Reactions of 1,6‐ and 1,7‐Bis(acylsilanes)
Author(s) -
Bouillon JeanPhilippe,
Portella Charles
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199907)1999:7<1571::aid-ejoc1571>3.0.co;2-4
Subject(s) - aldol reaction , chemistry , intramolecular force , stereoselectivity , lewis acids and bases , intramolecular reaction , aldol condensation , lewis acid catalysis , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A series of 1,6‐ and 1,7‐bis(acylsilanes) have been prepared using a strategy of substitution of dihalo derivatives with a synthetic equivalent of the trialkylsilylcarbonyl anion. These bis(acylsilanes) could easily be converted, under Lewis acid activation, into cis ‐β‐hydroxyacylsilanes or the corresponding α,β‐unsaturated derivatives, by means of a completely stereoselective intramolecular aldol reaction.