Acyclic Stereoselective Boron Alkylation Reactions for the Asymmetric Synthesis of β-Substituted α-Amino Acid Derivatives

Martin J. O'Donnell; Jeremy T. Cooper; Mary M. Mader

doi:10.1021/ja0298794

Acyclic Stereoselective Boron Alkylation Reactions for the Asymmetric Synthesis of β-Substituted α-Amino Acid Derivatives

Journal of the American Chemical Society ◽

10.1021/ja0298794 ◽

2003 ◽

Vol 125 (9) ◽

pp. 2370-2371 ◽

Cited By ~ 29

Author(s):

Martin J. O'Donnell ◽

Jeremy T. Cooper ◽

Mary M. Mader

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Alkylation Reactions

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Faculty Opinions recommendation of Catalytic enantio- and diastereoselective aldol reactions of glycine-derived silicon enolate with aldehydes: an efficient approach to the asymmetric synthesis of anti-beta-hydroxy-alpha-amino acid derivatives.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1020519.232639 ◽

2004 ◽

Author(s):

Carlos F Barbas

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Aldol Reactions ◽

Amino Acid Derivatives ◽

Efficient Approach ◽

Alpha Amino Acid

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Asymmetric Synthesis of New β,β-Difluorinated Cyclic Quaternary α-Amino Acid Derivatives

Organic Letters ◽

10.1021/ol070419v ◽

2007 ◽

Vol 9 (9) ◽

pp. 1841-1841

Author(s):

Santos Fustero ◽

Maria Sánchez-Roselló ◽

Vanessa Rodrigo ◽

Carlos del Pozo ◽

Juan F. Sanz-Cervera ◽

...

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives

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ChemInform Abstract: Catalytic Asymmetric Synthesis of Functionalized α,α-Disubstituted α-Amino Acid Derivatives from Racemic Unprotected α-Amino Acids via in situ Generated Azlactones.

ChemInform ◽

10.1002/chin.201242200 ◽

2012 ◽

Vol 43 (42) ◽

pp. no-no

Author(s):

Manuel Weber ◽

Wolfgang Frey ◽

Rene Peters

Keyword(s):

Amino Acids ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes: An Efficient Approach to the Asymmetric Synthesis ofanti-β-Hydroxy-α-Amino Acid Derivatives

Journal of the American Chemical Society ◽

10.1021/ja047597t ◽

2004 ◽

Vol 126 (30) ◽

pp. 9192-9193 ◽

Cited By ~ 52

Author(s):

Jun Kobayashi ◽

Masayuki Nakamura ◽

Yuichiro Mori ◽

Yasuhiro Yamashita ◽

Shū Kobayashi

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Aldol Reactions ◽

Amino Acid Derivatives ◽

Efficient Approach

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Asymmetric synthesis of α-amino-acid derivatives by alkylation of a chiral Schiff base

Journal of the Chemical Society Chemical Communications ◽

10.1039/c39760000136 ◽

1976 ◽

pp. 136-137 ◽

Cited By ~ 60

Author(s):

Shun-Ichi Yamada ◽

Tomei Oguri ◽

Takayuki Shioiri

Keyword(s):

Schiff Base ◽

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Chiral Schiff Base

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One-Pot Asymmetric Synthesis of β-Cyanohydroxymethyl α-Amino Acid Derivatives: Formation of Three Contiguous Stereogenic Centers

Organic Letters ◽

10.1021/ol027048x ◽

2002 ◽

Vol 4 (25) ◽

pp. 4519-4522 ◽

Cited By ~ 42

Author(s):

Shin-ichi Watanabe ◽

Armando Córdova ◽

Fujie Tanaka ◽

Carlos F. Barbas

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

One Pot ◽

Stereogenic Centers

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Asymmetric Synthesis of Oxindole-Derived Vicinal Tetrasubstituted Acyclic Amino Acid Derivatives by the Mannich-Type Reaction

The Journal of Organic Chemistry ◽

10.1021/acs.joc.0c00981 ◽

2020 ◽

Vol 85 (15) ◽

pp. 9661-9671 ◽

Cited By ~ 2

Author(s):

Ke-Qiang Hou ◽

Feng Zhou ◽

Xue-Ping Chen ◽

Yang Ge ◽

Albert S. C. Chan ◽

...

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Amino Acid Derivatives ◽

Type Reaction

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Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents

Heterocyclic Communications ◽

10.1515/hc-2019-0019 ◽

2019 ◽

Vol 25 (1) ◽

pp. 116-121

Author(s):

Wei Zhou ◽

Qingwei Xiao ◽

Yuanyuan Chang ◽

Qifa Liu ◽

Xiaohao Zang ◽

...

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Michael Addition ◽

Chiral Auxiliary ◽

Grignard Reagents ◽

Amino Acid Derivatives ◽

Catalyst Free ◽

Chemical Efficiency

AbstractHerein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.

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