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Synthesis of Diastereoenriched α ‐Aminomethyl Enaminones via a Brønsted Acid‐Catalyzed Asymmetric aza ‐Baylis‐Hillman Reaction of Chiral N ‐Phosphonyl Imines
Author(s) -
Liu Yangxue,
Ahmed Sultan,
Qin XiaoYan,
Rouh Hossein,
Wu Guanzhao,
Li Guigen,
Jiang Bo
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201901734
Subject(s) - imine , chemistry , chirality (physics) , catalysis , absolute configuration , enantioselective synthesis , combinatorial chemistry , brønsted–lowry acid–base theory , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , physics , chiral symmetry , quantum mechanics , nambu–jona lasinio model , quark
Abstract An effective chiral GAP methodology for preparing α ‐aminomethyl enaminones through a ( R )‐CSA‐catalyzed asymmetric aza ‐Baylis‐Hillman reaction is reported. Excellent yields and high diastereoselectivity could be obtained under mild conditions and convenient GAP techniques. The confirmations of the absolute configuration of N ‐phosphonyl imine and chiral enaminone by X‐ray diffraction provides an explicit explanation of the chirality mechanism for GAP chemistry.