Studies of intramolecular alkylidene carbene reactions; an approach to heterocyclic nucleoside bases |
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Authors: | Gerard HobleyKeith Stuttle Martin Wills |
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Affiliation: | a Department of Chemistry, University of Warwick, Gibbit Hill Road, Coventry CV4 7AL, UK b Aventis Pharma Ltd, Rainham Road South, Dagenham, Essex RM10 7XS, UK |
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Abstract: | A series of investigations into the applications of intramolecular cyclisations of alkylidene carbenes are described. The insertion reaction of the carbene generated from 1,4-di(tert-butyldimethylsilyloxy)-3-benzyloxy-butane-2-one to the benzylic position proceeded in good yield and a diastereoselectivity of 3.6:1. The corresponding insertion process of 1,4-di(tert-butyldimethylsilyloxy)-3-methyloxymethyl-butane-2-one gave a mixture of products, including one resulting from a competitive trapping of the carbene by the oxygen atom of a silyloxy group. |
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Keywords: | carbene alkylidene insertion ketone stereoselective cyclisation |
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