- Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives
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Optically active syn- or anti-β-substituted-α-amino acid derivatives are prepared in 94 to ≥99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride. Copyright
- O'Donnell, Martin J.,Cooper, Jeremy T.,Mader, Mary M.
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p. 2370 - 2371
(2007/10/03)
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- Stereocontrolled synthesis of serricornin
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Serricornin, the attractant pheromone of the cigarette beetle, is synthesized in high enantiomeric and diastereomeric purity via a series of reactions of asymmetric 2-(1-haloalkyl)-1,3,2-dioxaborolanes with Grignard reagents, which lead to the key intermediate ?,S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen-6-ol. Oxidative cleavage of the carbon-carbon double bond of ?S-(R*,R*,R*)!-2-ethyl-3,5-dimethyl-l-octen -6-ol with osmium tetroxide and sodium periodate yields serricornin.
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