Cu(i)/TF-BiphamPhos-catalyzed asymmetric Michael addition of cyclic ketimino esters to alkylidene malonates

Zhi-Yong Xue; Zhi-Min Song; Chun-Jiang Wang

doi:10.1039/c5ob00591d

Cu(i)/TF-BiphamPhos-catalyzed asymmetric Michael addition of cyclic ketimino esters to alkylidene malonates

Organic & Biomolecular Chemistry ◽

10.1039/c5ob00591d ◽

2015 ◽

Vol 13 (19) ◽

pp. 5460-5466 ◽

Cited By ~ 23

Author(s):

Zhi-Yong Xue ◽

Zhi-Min Song ◽

Chun-Jiang Wang

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Asymmetric Michael Addition ◽

Stereogenic Centers ◽

Efficient Construction

Cu(i)-catalyzed asymmetric Michael addition of cyclic ketimino esters with alkylidene malonates has been developed for efficient construction of β-branched α-amino acids containing adjacent quaternary and tertiary stereogenic centers in good yields with excellent diastereo-/enantioselectivities.

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ChemInform Abstract: An Asymmetric Michael Addition of α,α-Disubstituted Aldehydes to Maleimides Leading to a One-Pot Enantioselective Synthesis of Lactones Catalyzed by Amino Acids.

ChemInform ◽

10.1002/chin.201337096 ◽

2013 ◽

Vol 44 (37) ◽

pp. no-no

Author(s):

Christoforos G. Kokotos

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Enantioselective Synthesis ◽

One Pot ◽

Asymmetric Michael Addition

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One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein–Ponndorf–Verley Reduction

Angewandte Chemie International Edition ◽

10.1002/anie.200351915 ◽

2003 ◽

Vol 42 (37) ◽

pp. 4515-4517 ◽

Cited By ~ 25

Author(s):

Kiyoharu Nishide ◽

Minoru Ozeki ◽

Hideaki Kunishige ◽

Yukihiro Shigeta ◽

Pranab K. Patra ◽

...

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition ◽

Stereogenic Centers ◽

One Step

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Cover Feature: α‐Amino Acids and α,β‐Dipeptides Intercalated into Hydrotalcite: Efficient Catalysts in the Asymmetric Michael Addition Reaction of Aldehydes to N ‐Substituted Maleimides (Eur. J. Org. Chem. 37/2021)

European Journal of Organic Chemistry ◽

10.1002/ejoc.202101146 ◽

2021 ◽

Vol 2021 (37) ◽

pp. 5105-5105

Author(s):

José M. Landeros ◽

Carlos Cruz‐Hernández ◽

Eusebio Juaristi

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Addition Reaction ◽

Michael Addition Reaction ◽

Asymmetric Michael Addition

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Surface-Improved Asymmetric Michael Addition Catalyzed by Amino Acids Adsorbed on Laponite

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201701627 ◽

2018 ◽

Vol 360 (10) ◽

pp. 1992-2004 ◽

Cited By ~ 11

Author(s):

György Szőllősi ◽

Dániel Gombkötő ◽

Attila Zsolt Mogyorós ◽

Ferenc Fülöp

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Asymmetric Michael Addition

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ChemInform Abstract: Organocatalytic Asymmetric Michael Addition of Ethyl Nitroacetate to Enones Using Natural Amino Acids-Derived C1-Symmetric Chiral Primary-Secondary Diamines.

ChemInform ◽

10.1002/chin.201337060 ◽

2013 ◽

Vol 44 (37) ◽

pp. no-no

Author(s):

Yirong Zhou ◽

Qiang Liu ◽

Yuefa Gong

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Asymmetric Michael Addition ◽

Ethyl Nitroacetate ◽

Natural Amino Acids

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One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein—Ponndorf—Verley Reduction.

ChemInform ◽

10.1002/chin.200403025 ◽

2004 ◽

Vol 35 (3) ◽

Author(s):

Kiyoharu Nishide ◽

Minoru Ozeki ◽

Hideaki Kunishige ◽

Yukihiro Shigeta ◽

Pranab K. Patra ◽

...

Keyword(s):

Michael Addition ◽

Asymmetric Michael Addition ◽

Stereogenic Centers ◽

One Step

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Organocatalytic asymmetric Michael addition of ethyl nitroacetate to enones using natural amino acids-derived C1-symmetric chiral primary–secondary diamines

Tetrahedron Letters ◽

10.1016/j.tetlet.2013.04.005 ◽

2013 ◽

Vol 54 (23) ◽

pp. 3011-3014 ◽

Cited By ~ 12

Author(s):

Yirong Zhou ◽

Qiang Liu ◽

Yuefa Gong

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Asymmetric Michael Addition ◽

Ethyl Nitroacetate ◽

Natural Amino Acids

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An Asymmetric Michael Addition of α,α-Disubstituted Aldehydes to Maleimides Leading to a One-Pot Enantioselective Synthesis of Lactones Catalyzed by Amino Acids

Organic Letters ◽

10.1021/ol4008662 ◽

2013 ◽

Vol 15 (10) ◽

pp. 2406-2409 ◽

Cited By ~ 61

Author(s):

Christoforos G. Kokotos

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Enantioselective Synthesis ◽

One Pot ◽

Asymmetric Michael Addition

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ChemInform Abstract: Asymmetric Michael Addition of α-Fluoro-α-Nitro Esters to Nitroolefins: Towards Synthesis of α-Fluoro-α-Substituted Amino Acids.

ChemInform ◽

10.1002/chin.201526093 ◽

2015 ◽

Vol 46 (26) ◽

pp. no-no

Author(s):

Jacek Kwiatkowski ◽

Yixin Lu

Keyword(s):

Amino Acids ◽

Michael Addition ◽

Asymmetric Michael Addition ◽

Nitro Esters

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Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality

Chemical Communications ◽

10.1039/c5cc03203b ◽

2015 ◽

Vol 51 (52) ◽

pp. 10554-10557 ◽

Cited By ~ 28

Author(s):

Jianlin Zhang ◽

Yulong Zhang ◽

Lili Lin ◽

Qian Yao ◽

Xiaohua Liu ◽

...

Keyword(s):

Michael Addition ◽

Axial Chirality ◽

Asymmetric Michael Addition ◽

Efficient Construction ◽

Catalytic Asymmetric

The asymmetric Michael addition/desymmetrization reaction catalyzed by a N,N′-dioxide-Sc(iii) complex was realized, leading to the succinimides with two kinds of stereogenic elements—atom chirality and axial chirality in up to 99% yield, 99% ee and >19 : 1 d.r.

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