Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine

Mei;  Yin;  Miwa;  Moriwaki;  Abe;  Han;  Soloshonok

doi:10.3390/sym11040578

Convenient Asymmetric Synthesis of Fmoc-(S)-6,6,6-Trifluoro-Norleucine

Symmetry ◽

10.3390/sym11040578 ◽

2019 ◽

Vol 11 (4) ◽

pp. 578 ◽

Cited By ~ 18

Author(s):

Mei ◽

Yin ◽

Miwa ◽

Moriwaki ◽

Abe ◽

...

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Total Yield ◽

Enantiomeric Purity ◽

Alkylation Reaction ◽

Target Amino Acid

In this work we report a convenient asymmetric synthesis of Fmoc-(S)-6,6,6-trifluoro-norleucine via alkylation reaction of chiral glycine equivalent. The target amino acid of 99% enantiomeric purity was prepared with 82.4% total yield (three steps).

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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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An asymmetric synthesis of 5-methoxy-3-substituted acids and their related lactones in high enantiomeric purity

Tetrahedron Letters ◽

10.1016/s0040-4039(00)78086-5 ◽

1976 ◽

Vol 17 (23) ◽

pp. 1947-1950 ◽

Cited By ~ 22

Author(s):

A.I. Meyers ◽

Charles E. Whitten

Keyword(s):

Asymmetric Synthesis ◽

Enantiomeric Purity

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Sequential diastereoselective addition and allylic azide isomerization of syn- and anti-.alpha.-azido-.beta.-(dimethylphenylsilyl)-(E)-hex-4-enoates with acetals: asymmetric synthesis of .gamma.-hydroxy-.alpha.-amino acid synthons

The Journal of Organic Chemistry ◽

10.1021/jo00041a002 ◽

1992 ◽

Vol 57 (15) ◽

pp. 4063-4064 ◽

Cited By ~ 18

Author(s):

James S. Panek ◽

Michael Yang ◽

Itzhak Muler

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Diastereoselective Addition ◽

Alpha Amino Acid

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Asymmetric Synthesis of Unnatural Amino Acid-containing Peptides via Direct Asymmetric Reaction of Peptidyl Compounds

YAKUGAKU ZASSHI ◽

10.1248/yakushi.18-00143 ◽

2018 ◽

Vol 138 (11) ◽

pp. 1371-1379

Author(s):

Tsubasa Inokuma

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Unnatural Amino Acid ◽

Asymmetric Reaction

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Asymmetric synthesis of homochiral differentially protected bis-β-amino acid scaffolds

Tetrahedron ◽

10.1016/s0040-4020(02)00369-1 ◽

2002 ◽

Vol 58 (23) ◽

pp. 4629-4642 ◽

Cited By ~ 17

Author(s):

Steven D Bull ◽

Stephen G Davies ◽

Paul M Roberts ◽

Edward D Savory ◽

Andrew D Smith

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis

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Asymmetric synthesis XVI. Enantiomerically pure substituted cyclopropane amino acid precursors via the cn(R,S) method

Tetrahedron Letters ◽

10.1016/0040-4039(88)85150-5 ◽

1988 ◽

Vol 29 (27) ◽

pp. 3315-3318 ◽

Cited By ~ 12

Author(s):

David J. Aitken ◽

Jacques Royer ◽

Henri-Philippe Husson

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Enantiomerically Pure ◽

Amino Acid Precursors

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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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Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization

Chemistry - A European Journal ◽

10.1002/chem.201604207 ◽

2016 ◽

Vol 22 (46) ◽

pp. 16429-16432 ◽

Cited By ~ 12

Author(s):

Yuki Kaji ◽

Naohiro Uemura ◽

Yoshio Kasashima ◽

Hiroki Ishikawa ◽

Yasushi Yoshida ◽

...

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Acid Derivative ◽

Michael Addition ◽

Amino Acid Derivative

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Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

Molecules ◽

10.3390/molecules191219516 ◽

2014 ◽

Vol 19 (12) ◽

pp. 19516-19531 ◽

Cited By ~ 1

Author(s):

Mario Simirgiotis ◽

Javier Vallejos ◽

Carlos Areche ◽

Beatriz Sepúlveda

Keyword(s):

Amino Acid ◽

Asymmetric Synthesis ◽

Hydroxy Amino Acid ◽

Hydroxy Amino

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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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