Construction of α, α‐disubstituted α‐Amino Acid Derivatives via aza‐Morita‐Baylis‐Hillman Reactions of 2‐Aminoacrylates with Activated Olefins. Issue 4 (3rd February 2020)

• Record Type: Journal Article
• Authors: Gui, Hou‐Ze; Jangra, Harish; Mao, Ben; Wang, Tian‐Yu; Yi, Heng; Xu, Qin; Wei, Yin; Zipse, Hendrik; Shi, Min
• Is Part Of: ChemCatChem. Volume 12:Issue 4(2020)
• Page Start: 1143
• Page End: 1147
• Publication Date: 2020-02-03
• Subjects: phosphine catalysis -- aza-MBH reaction -- α, α-disubstituted -- α-amino acids -- methyl anion affinity values; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201901987
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: 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. Abstract : Alpha Amino Acids : A novel tertiary phosphine catalyzed aza‐MBH reaction of 2‐aminoacrylates with MVK was disclosed, affording the corresponding α‐AAs derivatives under mild conditions.