e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron: Asymmetry

Parallel synthesis of homochiral β-amino acids

SG Davies, AW Mulvaney, AJ Russell, AD Smith

Index: Davies, Stephen G.; Mulvaney, Andrew W.; Russell, Angela J.; Smith, Andrew D. Tetrahedron Asymmetry, 2007 , vol. 18, # 13 p. 1554 - 1566

Full Text: HTML

Citation Number: 37

Abstract

The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl) amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α, β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and ...

1,1-Dimethylethyl (I(2)S)-I(2)-amino-3,4-dimethoxybenzenepropanoate Structure

1,1-Dimethyleth...

~97%

3-Amino-3-(3,4-dimethoxyphenyl)propanoic acid Structure

3-Amino-3-(3,4-...

tert-Butyl (3R)-3-amino-3-phenylpropanoate Structure

tert-Butyl (3R)...

~96%

H-DL-β-Phe-OH Structure

N/A Structure

~94%

(R)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID Structure

(R)-3-AMINO-3-(...

(E)-tert-butyl 3-(4-(benzyloxy)phenyl)acrylate Structure

(E)-tert-butyl ...

~%

(R)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID Structure

(R)-3-AMINO-3-(...

tert-butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoate Structure

tert-butyl (3R,...

~%

(R)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID Structure

(R)-3-AMINO-3-(...

4-(Benzyloxy)benzaldehyde Structure

4-(Benzyloxy)be...

~%

(R)-3-AMINO-3-(4-HYDROXYPHENYL)PROPANOIC ACID Structure

(R)-3-AMINO-3-(...

N/A Structure

~96%

3-Amino-3-(4-methoxyphenyl)propanoic acid Structure

3-Amino-3-(4-me...

2-Methyl-2-propanyl (3R)-3-{benzyl[(1S)-1-phenylethyl]amino}-3-ph enylpropanoate Structure

2-Methyl-2-prop...

~88%

tert-Butyl (3R)-3-amino-3-phenylpropanoate Structure

tert-Butyl (3R)...

2-Propenoic acid,3-phenyl-, 1,1-dimethylethyl ester Structure

2-Propenoic aci...

~%

tert-Butyl (3R)-3-amino-3-phenylpropanoate Structure

tert-Butyl (3R)...

tert-Butyl 2-(diethoxyphosphoryl)acetate Structure

tert-Butyl 2-(d...

~%

tert-Butyl (3R)-3-amino-3-phenylpropanoate Structure

tert-Butyl (3R)...

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate Structure

tert-butyl (3S,...

~88%

tert-Butyl-(3S)-3-amino-3-phenylpropanoate Structure

tert-Butyl-(3S)...

2-Methyl-2-propanyl 3-aminobutanoate Structure

2-Methyl-2-prop...

~98%

UNII:4282SA5CTS Structure

UNII:4282SA5CTS

tert-Butyl (3S)-3-aminobutanoate Structure

tert-Butyl (3S)...

~89%

(S)-3-Aminobutanoic acid Structure

(S)-3-Aminobuta...

tert-Butyl (3R)-3-Amino-5-methylhexanoate Structure

tert-Butyl (3R)...

~97%

(R)-3-Amino-5-methylhexanoic acid Structure

(R)-3-Amino-5-m...

tert-butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)-5-methylhexanoate Structure

tert-butyl (3R,...

~%

(R)-3-Amino-5-methylhexanoic acid Structure

(R)-3-Amino-5-m...

tert-Butyl 2-(diethoxyphosphoryl)acetate Structure

tert-Butyl 2-(d...

ch3cho Structure

~95%

tert-Butyl Crotonate Structure

tert-Butyl Crotonate

2-Methyl-2-propanyl (2E)-5-methyl-2-hexenoate Structure

2-Methyl-2-prop...

~%

(R)-3-Amino-5-methylhexanoic acid Structure

(R)-3-Amino-5-m...

tert-Butyl 2-(diethoxyphosphoryl)acetate Structure

tert-Butyl 2-(d...

~%

2-Methyl-2-propanyl (3R)-3-{benzyl[(1S)-1-phenylethyl]amino}-3-ph enylpropanoate Structure

2-Methyl-2-prop...

Benzaldehyde Structure

~%

2-Methyl-2-propanyl (3R)-3-{benzyl[(1S)-1-phenylethyl]amino}-3-ph enylpropanoate Structure

2-Methyl-2-prop...

tert-Butyl Crotonate Structure

tert-Butyl Crotonate

~%

2-Methyl-2-propanyl 3-aminobutanoate Structure

2-Methyl-2-prop...

tert-Butyl 2-(diethoxyphosphoryl)acetate Structure

tert-Butyl 2-(d...

~%

2-Methyl-2-propanyl 3-aminobutanoate Structure

2-Methyl-2-prop...

Octanal Structure

tert-Butyl 2-(diethoxyphosphoryl)acetate Structure

tert-Butyl 2-(d...

~90%

tert-butyl dec-2-enoate Structure

tert-butyl dec-...

Parallel synthesis of homochiral β-amino acids

[Tetrahedron Asymmetry, , vol. 18, # 13 p. 1554 - 1566]

Parallel synthesis of homochiral β-amino acids

[Tetrahedron Asymmetry, , vol. 18, # 13 p. 1554 - 1566]

Parallel synthesis of homochiral β-amino acids

[Tetrahedron Asymmetry, , vol. 18, # 13 p. 1554 - 1566]