Camphor-Derived Alcohols: An Anomalous Reaction of 3-Hydroxycamphor and the Influence of Internal Alkoxides on the Alkylation Stereochemistry of Glycinate Imines

Article abstract of DOI:10.1016/S0040-4020(01)89491-6

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 norcamphor and tert. butyl glycinate gave no stereoselection.Alkylation of the imine from 10-hydroxymethylcamphor 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 effected in 71percent yield.