In this paper, we report the first examples of Lewis acid and mercuric trifluoroacetate promoted cyclizations of 1,6-dienes containing an allylsilane moiety. Mercuric trifluoroacetate has been proved to be the reagent of choice leading to methylenecyclohexane derivatives in good yields and with complete regioselectivity albeit with poor diastereoselectivity. Using this methodology a stereodivergent synthesis of enantiomerically pure (−)-(2S,6R)-cis-γ-irone and (−)-(2S,6S)- trans-γ-irone, two precious aroma constituents, has been accomplished. This represents an innovative approach with respect to previous syntheses of γ-irones.
Electrophilic Cyclization of 1,6-Dienes Containing an Allylsilane Moiety - Enantioselective Synthesis of cis- and trans-γ-Irone / Stephen Beszant, Elios Giannini, Giuseppe Zanoni, Giovanni Vidari. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2003:20(2003 Oct 17), pp. 3958-3968. [10.1002/ejoc.200300276]
Electrophilic Cyclization of 1,6-Dienes Containing an Allylsilane Moiety - Enantioselective Synthesis of cis- and trans-γ-Irone
Elios Giannini;
2003
Abstract
In this paper, we report the first examples of Lewis acid and mercuric trifluoroacetate promoted cyclizations of 1,6-dienes containing an allylsilane moiety. Mercuric trifluoroacetate has been proved to be the reagent of choice leading to methylenecyclohexane derivatives in good yields and with complete regioselectivity albeit with poor diastereoselectivity. Using this methodology a stereodivergent synthesis of enantiomerically pure (−)-(2S,6R)-cis-γ-irone and (−)-(2S,6S)- trans-γ-irone, two precious aroma constituents, has been accomplished. This represents an innovative approach with respect to previous syntheses of γ-irones.
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