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Construction of α,α‐disubstituted α‐Amino Acid Derivatives via aza‐Morita‐Baylis‐Hillman Reactions of 2‐Aminoacrylates with Activated Olefins
Author(s) -
Gui HouZe,
Jangra Harish,
Mao Ben,
Wang TianYu,
Yi Heng,
Xu Qin,
Wei Yin,
Zipse Hendrik,
Shi Min
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901987
Subject(s) - chemistry , baylis–hillman reaction , amino acid , organic chemistry , catalysis , combinatorial chemistry , stereochemistry , medicinal chemistry , biochemistry
A useful and convenient strategy for the synthesis of α,α‐disubstituted α‐amino acid (α‐AA) derivatives via aza‐Morita‐Baylis‐Hillman reaction of 2‐aminoacrylates with activated olefins has been developed. A variety of α‐AA derivatives containing an α‐amino tertiary center were synthesized in good to excellent yields. The kinetic profiles and calculated methyl anion affinity (MAA) values were employed to rationalize the reactivities of different Michael acceptors used in the reaction.