(R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate: chiral building block for the synthesis of optically active α-substituted α-amino acid derivatives

Hiroaki Miyaoka; Makoto Yamanishi; Ayako Hoshino; Atsushi Kinbara

doi:10.1016/j.tet.2006.02.022

(R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate: chiral building block for the synthesis of optically active α-substituted α-amino acid derivatives

Tetrahedron ◽

10.1016/j.tet.2006.02.022 ◽

2006 ◽

Vol 62 (17) ◽

pp. 4103-4109 ◽

Cited By ~ 21

Author(s):

Hiroaki Miyaoka ◽

Makoto Yamanishi ◽

Ayako Hoshino ◽

Atsushi Kinbara

Keyword(s):

Amino Acid ◽

Building Block ◽

Optically Active ◽

Amino Acid Derivatives ◽

Chiral Building Block

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UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽

10.1055/a-1736-4388 ◽

2022 ◽

Author(s):

Dishu Zeng ◽

Tianbao Yang ◽

Niu Tang ◽

Wei Deng ◽

Jiannan Xiang ◽

...

Keyword(s):

Amino Acid ◽

Organic Synthesis ◽

Efficient Method ◽

Building Block ◽

Room Temperature ◽

Uv Light ◽

Amino Acid Derivatives ◽

One Pot ◽

Plausible Mechanism ◽

High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

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ChemInform Abstract: Optically Active Aromatics Possessing Helical Chirality: One-Pot Synthesis, Optical Resolution and Crystal Structure of 13,14-Dimethyldibenzo[b,j][4,7]phenanthroline and Its Dihydro Form as a Novel Chiral Building Block.

ChemInform ◽

10.1002/chin.199850173 ◽

2010 ◽

Vol 29 (50) ◽

pp. no-no

Author(s):

Y. TANAKA ◽

A. SEKITA ◽

H. SUZUKI ◽

M. YAMASHITA ◽

T. OSHIKAWA ◽

...

Keyword(s):

Crystal Structure ◽

Building Block ◽

Optical Resolution ◽

Optically Active ◽

One Pot ◽

One Pot Synthesis ◽

Chiral Building Block ◽

Helical Chirality

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Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process

Chemical Communications ◽

10.1039/c2cc30799e ◽

2012 ◽

Vol 48 (39) ◽

pp. 4713 ◽

Cited By ~ 22

Author(s):

Zhi-Cong Geng ◽

Ning Li ◽

Jian Chen ◽

Xiao-Fei Huang ◽

Bin Wu ◽

...

Keyword(s):

Amino Acid ◽

Ring Opening ◽

Optically Active ◽

Enantioselective Synthesis ◽

Amino Acid Derivatives ◽

Opening Process

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Synthesis of Optically Active 2,3-Disubstituted Indoline Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles

Synlett ◽

10.1055/s-0036-1591722 ◽

2018 ◽

Vol 29 (04) ◽

pp. 530-536 ◽

Cited By ~ 4

Author(s):

Takashi Ikawa ◽

Shuji Akai ◽

Yuta Sumii ◽

Shigeaki Masuda ◽

Ding Wang ◽

...

Keyword(s):

Amino Acid ◽

Cycloaddition Reaction ◽

Optically Active ◽

Amino Acid Derivatives ◽

Cycloaddition Reactions

We report a method for synthesizing optically active 2,3-disubstituted indolines by the cycloaddition reaction of benzynes with various 4-[(4-toluenesulfonyl)amino]-(E)-but-2-enenitriles, which are readily prepared from the corresponding l-amino acid derivatives.

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Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternaryα-Amino Acid Derivatives

Angewandte Chemie International Edition ◽

10.1002/anie.200460158 ◽

2004 ◽

Vol 43 (34) ◽

pp. 4476-4478 ◽

Cited By ~ 171

Author(s):

Wei Zhuang ◽

Steen Saaby ◽

Karl Anker Jørgensen

Keyword(s):

Amino Acid ◽

Optically Active ◽

Amino Acid Derivatives ◽

Mannich Reactions

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ChemInform Abstract: Enantiomer Separation of (R,S)-2-(tert-Butyl)-3-methyl-4-imidazolidinone, a Chiral Building Block for Amino Acid Synthesis.

Chemischer Informationsdienst ◽

10.1002/chin.198631106 ◽

1986 ◽

Vol 17 (31) ◽

Author(s):

R. FITZI ◽

D. SEEBACH

Keyword(s):

Amino Acid ◽

Building Block ◽

Enantiomer Separation ◽

Acid Synthesis ◽

Amino Acid Synthesis ◽

Tert Butyl ◽

Chiral Building Block

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ChemInform Abstract: A Convenient Synthesis of Racemic and Optically Active 1-Aza-1,3-dienes Derived from γ-Amino Esters: Reduction to α,β-Unsaturated and Saturated γ-Amino Acid Derivatives.

ChemInform ◽

10.1002/chin.200130078 ◽

2010 ◽

Vol 32 (30) ◽

pp. no-no

Author(s):

Francisco Palacios ◽

Domitila Aparicio ◽

Jesus Garcia ◽

Encina Rodriguez ◽

Alvaro Fernandez-Acebes

Keyword(s):

Amino Acid ◽

Optically Active ◽

Amino Acid Derivatives ◽

Amino Esters ◽

Convenient Synthesis

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Catalytic Asymmetric Mono-Fluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-Hydroxy and β-Fluoro-α-Amino Acid Derivatives

Angewandte Chemie ◽

10.1002/ange.201201303 ◽

2012 ◽

Vol 124 (19) ◽

pp. 4659-4663 ◽

Cited By ~ 16

Author(s):

Shoko Suzuki ◽

Yuki Kitamura ◽

Sylvain Lectard ◽

Yoshitaka Hamashima ◽

Mikiko Sodeoka

Keyword(s):

Amino Acid ◽

Optically Active ◽

Amino Acid Derivatives ◽

Keto Esters ◽

Catalytic Asymmetric

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Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternaryα-Amino Acid Derivatives

Angewandte Chemie ◽

10.1002/ange.200460158 ◽

2004 ◽

Vol 116 (34) ◽

pp. 4576-4578 ◽

Cited By ~ 70

Author(s):

Wei Zhuang ◽

Steen Saaby ◽

Karl Anker Jørgensen

Keyword(s):

Amino Acid ◽

Optically Active ◽

Amino Acid Derivatives ◽

Mannich Reactions

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An asymmetric synthesis of carboxylic acid derivatives, including lactic acid and α-amino acid derivatives, from optically active 1-chlorovinyl p-tolyl sulfoxides and ester lithium enolates with creation of chirality at the α-position

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2007.07.033 ◽

2007 ◽

Vol 18 (16) ◽

pp. 1934-1947 ◽

Cited By ~ 9

Author(s):

Masahiro Kido ◽

Shimpei Sugiyama ◽

Tsuyoshi Satoh

Keyword(s):

Lactic Acid ◽

Amino Acid ◽

Carboxylic Acid ◽

Asymmetric Synthesis ◽

Optically Active ◽

Amino Acid Derivatives ◽

Lithium Enolates

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(R)-4-Hydroxymethyl-2-phenyl-4,5-dihydrooxazol-4-ylmethyl acetate: chiral building block for the synthesis of optically active α-substituted α-amino acid derivatives

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

ChemInform Abstract: Optically Active Aromatics Possessing Helical Chirality: One-Pot Synthesis, Optical Resolution and Crystal Structure of 13,14-Dimethyldibenzo[b,j][4,7]phenanthroline and Its Dihydro Form as a Novel Chiral Building Block.

Enantioselective synthesis of optically active cis-β-thio-α-amino acid derivatives through an organocatalytic cascade thio-Michael/ring opening process

Synthesis of Optically Active 2,3-Disubstituted Indoline ­Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles

Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternaryα-Amino Acid Derivatives

ChemInform Abstract: Enantiomer Separation of (R,S)-2-(tert-Butyl)-3-methyl-4-imidazolidinone, a Chiral Building Block for Amino Acid Synthesis.

ChemInform Abstract: A Convenient Synthesis of Racemic and Optically Active 1-Aza-1,3-dienes Derived from γ-Amino Esters: Reduction to α,β-Unsaturated and Saturated γ-Amino Acid Derivatives.

Catalytic Asymmetric Mono-Fluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-Hydroxy and β-Fluoro-α-Amino Acid Derivatives

Direct Organocatalytic Enantioselective Mannich Reactions of Ketimines: An Approach to Optically Active Quaternaryα-Amino Acid Derivatives

An asymmetric synthesis of carboxylic acid derivatives, including lactic acid and α-amino acid derivatives, from optically active 1-chlorovinyl p-tolyl sulfoxides and ester lithium enolates with creation of chirality at the α-position

Synthesis of Optically Active 2,3-Disubstituted Indoline Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles