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Synlett 2003(8): 1201-1203
DOI: 10.1055/s-2003-39888
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Reductive Cleavage of 1,3-Dithiane Systems Anchored on Polymers Useful for Supported Organic Syntheses

Vincenzo Bertini*a, Francesco Lucchesinia, Marco Poccia, Silvana Alfeia, Angela De Munnob
a Dipartimento di Chimica e Tecnologie Farmaceutiche e Alimentari, Università di Genova, Via Brigata Salerno, 16147 Genova, Italy
e-Mail: bertini@dictfa.unige.it;
b Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento 35, 56126 Pisa, Italy
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Publication History

Received 28 March 2003
Publication Date:
11 June 2003 (online)

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Abstract

Completely odourless reductions of ketones to alkanes through condensation with 1,3-propanedithiol copolymers and cleavage of the formed 1,3-dithiane units with sodium and ammonia or tributyltin hydride and AIBN, useful as a new synthetic methodology for combinatorial chemistry, is reported. Selective reductions of ketones in presence of an ester or a second ketone group are exemplified.

Key words

supported organic synthesis - dithiane reduction - ketone reduction - polymeric dithianes - polymeric dithiols