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Start Over Author "Luca C. Matassa" Topic alkylation
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2. Camphor-derived alcohols: An anomalous reaction of 3-hydroxycamphor and the influence of internal alkoxides on the alkylation stereochemistry of glycinate imines

Author

Luca C. Matassa, Kenneth C. Cassidy, and John M. McIntosh

Subjects
Bicyclic molecule, Chemistry, Stereochemistry, Organic Chemistry, Imine, Norcamphor, Alkylation, Biochemistry, Benzaldehyde, chemistry.chemical_compound, Camphor, Drug Discovery, Organic chemistry, Aldol condensation, Stereoselectivity
Abstract

Attempted imine formation between 3-hydroxycamphor and tert. butyl glycinate led to 8 the substitution product at the 3-position. Zinc-acetic acid treatment of 8 afforded 3-acetoxycamphor. Alkylation of the imine from from norcamphor and tert. butyl glycinate gave no stereoselection. Alkylation of the imine from from 10-hytdroxymethylcamphor and tert. butyl glycinate gave stereoselectivities inferior to those obtained from the imine of camphor itself ( 1 ) but aldol condensation with benzaldehyde, a reaction not possible with 1, was affected in 71% yield.

Published
1989
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