Expedient Synthesis of Chiral 1,2- and 1,4-Diamines: Protecting Group Dependent Regioselectivity in Direct Organocatalytic Asymmetric Mannich Reactions
Authors:
- 1 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (13) , 2839-2842
Abstract
Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an l-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones.Keywords
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