Stereocontrolled α-Alkylation of Oxime Ether Derived from Terpene: Efficient Synthesis of New Chiral γ- and δ-Amino Alcohols

Abstract

The alkylation of (+)-nopinone oxime ether with various electrophiles afforded the corresponding adduct with a total stereoselectivity. Further reduction of the oxime ether afforded an easily access to new chiral γ-and δ-amino alcohols of high interest for catalysis and asymmetric synthesis.

Key words

oxime ether - (+)-nopinone - stereocontrolled alkylation - amino alcohols

References and Notes

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7

Crystallographic data for the structural have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 665258, 298980, and 653068 for compounds 9a, 11c, and 10o, respectively. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: [phone]; e-mail: [e-mail] or www: http://www.ccdc.cam.ac.uk].