Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins

Gui, Hou-Ze1; Jangra, Harish4; Mao, Ben1; Wang, Tian-Yu1; Yi, Heng1; Xu, Qin1; Wei, Yin2; Zipse, Hendrik4; Shi, Min1,2,3

2020

10.1002/cctc.201901987

ChemCatChem   影响因子和分区

18673899

1867-3899

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.
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

phosphine catalysis aza-MBH reaction alpha,alpha-disubstituted alpha-amino acids methyl anion affinity values

SCI ; EI

英语

其他

National Basic Research Program of China (973 Program)[973)-2015CB856603] ; Fundamental Research Funds for the Central Universities[222201717003] ; Chinese Academy of Sciences[XDB20000000] ; National Natural Science Foundation of China[21772037]

Chemistry

Chemistry, Physical

WOS:000510555600001

Wiley Blackwell

20200608139568

Amino acids ; Olefins ; Phosphorus compounds ; Rate constants

Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry & Molecular Engineering, East China University of Science and Technology, Meilong Road No. 130, Shanghai; 200237, China
2.State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Linglin Lu, Shanghai; 200032, China
3.Shenzhen Grubbs Institute, Southern University of Science and Technology Shenzhen, Guangdong; 518000, China
4.Department of Chemistry, LMU München, Butenandtstrasse 5–13, München; 81377, Germany

Gui, Hou-Ze,Jangra, Harish,Mao, Ben,et al. Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins[J]. ChemCatChem,2020,12(4):1143-1147.

Gui, Hou-Ze.,Jangra, Harish.,Mao, Ben.,Wang, Tian-Yu.,Yi, Heng.,...&Shi, Min.(2020).Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins.ChemCatChem,12(4),1143-1147.

Gui, Hou-Ze,et al."Construction of α,α-disubstituted α-Amino Acid Derivatives via aza-Morita-Baylis-Hillman Reactions of 2-Aminoacrylates with Activated Olefins".ChemCatChem 12.4(2020):1143-1147.