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Synlett 2000; 2000(3): 323-326
DOI: 10.1055/s-2000-6533
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Diastereoselective Additions of Nucleophiles to Hindered α-Trimethylsilyloxy Aldehydes

Damien Bourgeois* , Gourhari Maiti, Ange Pancrazi, Joëlle Prunet
  • *Laboratoire de Synthèse Organique, associé au CNRS, Ecole Polytechnique, DCSO, 91128 Palaiseau, France; Fax (33) 1 69 33 30 10; E-mail: Joelle.Prunet@polytechnique.fr
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Publication Date:
31 December 2000 (online)

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High diastereoselectivity was observed for the additions of hindered nucleophiles such as 6c to hindered α-trimethylsilyloxyaldehydes 5 and 10, leading to trans-diols. Concomitant silyl transfer to the incipient secondary alcohol could explain this unusual selectivity.

diastereoselectivity - Shapiro reaction - vinyllithium - hindered aldehyde - taxol