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Highly Diastereo‐ and Enantioselective Synthesis of α‐Spiro‐δ‐lactams by an Organocascade Reaction
Author(s) -
Zhang Kaiheng,
Meazza Marta,
Dočekal Vojtěch,
Light Mark E.,
Veselý Jan,
Rios Ramon
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700193
Subject(s) - enantioselective synthesis , enantiopure drug , chemistry , stereocenter , annulation , hemiaminal , aldehyde , catalysis , michael reaction , amine gas treating , organocatalysis , organic chemistry , stereochemistry , combinatorial chemistry
An asymmetric synthesis of α‐spiro‐δ‐lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β‐ketoamide to an α,β‐unsaturated aldehyde, catalyzed by a secondary amine catalyst, and is followed by hemiaminal annulation. Optically enantiopure compounds with three stereogenic centres are obtained in good yields and excellent selectivities (up to >20:1 dr and up to >99 % ee ).