Premium
Asymmetric Tandem Conjugate Addition–Aldol Condensation with N ‐Acryloyloxazolidines Derived from 2‐Phenylglycinol
Author(s) -
ZelocualtecatlMontiel Iván,
GarcíaÁlvarez Fernando,
Juárez Jorge R.,
Orea Laura,
Gnecco Dino,
Mendoza Angel,
Chemla Fabrice,
Ferreira Franck,
Jackowski Olivier,
Aparicio David M.,
PerezLuna Alejandro,
Terán Joel L.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600501
Subject(s) - chemistry , aldol reaction , enantiopure drug , aldol condensation , moiety , diethylzinc , chiral auxiliary , enantioselective synthesis , hemiaminal , tandem , conjugate , stereochemistry , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , composite material
The tandem 1,4‐addition–aldol condensation reaction of diethylzinc, α,β‐unsaturated chiral enantiopure oxazolidines derived from 2‐phenylglycinol, and carbonyl compounds is disclosed. The reaction proceeds through a radical‐polar crossover mechanism involving the aldol condensation of a trisubstituted zinc enolate through a Zimmerman–Traxler transition state. Installation of a 2‐pyridine moiety at the hemiaminal position of the chiral auxiliary allows obtaining both excellent asymmetric induction and diastereoselectivity (up to >90 % de ). The developed protocol is suitable for aromatic and aliphatic aldehydes, as well as ketones.