Tetrahedron Letters p. 6845 - 6848 (1999)
Update date:2022-08-03
Topics: Synthesis Deprotonation Aldehyde Ketone Protecting group Stereoselectivity Functional group nucleophilic Stereoisomer Enolate Side reaction β-hydroxy carbonyl compound
Carda, Miguel
Falomir, Eva
Murga, Juan
Castillo, Encarnacion
Gonzalez, Florenci
Marco, J. Alberto
Boron aldol additions of 1-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 syn/anti 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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