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Boron aldol additions with erythrulose derivatives: dependence of stereoselectivity on the type of protecting group

✍ Scribed by Miguel Carda; Eva Falomir; Juan Murga; Encarnación Castillo; Florenci González; J. Alberto Marco

Book ID: 104262162
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 254 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01380-5

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✦ Synopsis

Boron aldol additions of l-O-silylated 3,4-di-O-benzyl-and 3,4-di-O-benzoyl-L-erythrulose and achiral aldehydes using dicyclohexylboron chloride have been investigated. The dibenzyl derivative gave syn/syn stereoisomers with high stereoselectivity, whereas the dibenzoyl derivative gave synlanti stereoisomers. It is believed that, while the dibenzoyl erythrulose gives rise to the E enolate in the presence of dicyclohexylboron chloride, as usually observed with this reagent, only the Z enolate is formed in the case of the dibenzyl derivative.

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