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On the regioselectivity and diastereoselectivity of ACC hydrazone alkylation

Author:
Huynh, Uyen, Uddin, Md. Nasir, Wengryniuk, Sarah E., McDonald, Stacey L., Coltart, Don M.
Source:
Tetrahedron 2017 v.73 no.5 pp. 432-436
ISSN:
0040-4020
Subject:
alkylation, chemical structure, diastereoselectivity, hydrazones, regioselectivity
Abstract:
The asymmetric α-allylation of 3-pentanone using several different N-amino cyclic carbamate (ACC) auxiliaries is described. The level of asymmetric induction was found to range from er = 93:7 to er = 99:1. The factors that lead to compromised selectivity for the various auxiliaries have been determined. Significantly, we have established that using the easily accessible and inexpensive valine-derived ACC auxiliary, it is possible to obtain synthetically useful levels of asymmetric induction (er = 96:4).
Agid:
6097541