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The Peterson Olefination Using the tert-Butyldiphenylsilyl Group: Stereoselective Synthesis of Di- and Trisubstituted Alkenes

Asunción Barbero*, Yolanda Blanco, Carlos García, Francisco J. Pulido

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, E-47011 Valladolid, Spain, Email:

A. Barbero, Y. Blanco, C. Garcia, Synthesis, 2000, 1223-1228.

DOI: 10.1055/s-2000-6409

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The reaction of α-tert-butyldiphenylsilyl carbonyl compounds with organometallics leads with a high diastereoselectivity to erythro-β-hydroxysilanes, which under acidic or basic elimination conditions give E or Z di- and trisubstituted alkenes.

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Key Words

Peterson Olefination, elimination, stereoselective synthesis, alkenes, silicon, pyridinium chlorochromate

ID: J66-Y2002-350