| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347979 | Tetrahedron: Asymmetry | 2007 | 13 Pages |
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 selectivities with minimal purification involved in each step of the reaction protocol.
Graphical abstractThe 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 are 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 selectivities.Figure optionsDownload full-size imageDownload as PowerPoint slide
tert-Butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)-butanoateC23H31NO2[α]D25=-5.2 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,αR)
tert-Butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)-5-methylhexanoateC26H37NO2[α]D25=+3.2 (c 1.6, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,αR)
tert-Butyl (3R,αR)-3-(N-benzyl-N-α-methylbenzylamino)decanoateC29H43NO2[α]D25=+6.4 (c 2.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,αR)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-methoxyphenyl)propanoateC29H35NO3[α]D25=+2.0 (c 2.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3-methoxyphenyl)propanoateC29H35NO3[α]D25=+3.3 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(2-methoxyphenyl)propanoateC29H35NO3[α]D25=-13.7 (c 2.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,αS)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3,5-dimethoxyphenyl)propanoateC30H37NO4[α]D25=+1.8 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3,5-dimethoxyphenyl)propanoateC30H37NO4[α]D25=+1.0 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(2,4-dimethoxyphenyl)propanoateC30H37NO4[α]D25=+8.6 (c 1.0, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-phenylpropanoateC28H33NO2[α]D25=+7.3 (c 0.8, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,αR)
tert-Butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-biphenyl)propanoateC34H37NO2[α]D25=+1.7 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (3R,αS)
tert-Butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3-piperon-3-yl)propanoateC29H33NO4[α]D25=-6.3 (c 1.5, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(3R,αS)
tert-Butyl (3S,αR)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3-benzyloxyphenyl)propanoateC35H39NO3[α]D25=+2.7 (c 1.1, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(3S,αR)
tert-Butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(4-benzyloxyphenyl)propanoateC35H39NO3[α]D25=-2.1 (c 1.4, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(3R,αS)
tert-Butyl (3R,αS)-3-(N-benzyl-N-α-methylbenzylamino)-3-(3,4-di-benzyloxyphenyl)propanoateC42H45NO4[α]D25=+2.2 (c 2.3, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(3R,αS)
tert-Butyl (R)-3-aminobutanoateC8H17NO2[α]D25=-22.2 (c 0.5, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (S)-3-amino-5-methylhexanoateC11H23NO2[α]D25=+21.2 (c 2.9, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(S)
tert-Butyl (R)-3-aminodecanoateC14H29NO2[α]D25=-11.3 (c 1.3, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (S)-3-amino-3-(4-methoxyphenyl)propanoateC14H21NO3[α]D25=+16.5 (c 1.4, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(S)
tert-Butyl (S)-3-amino-3-(3-methoxyphenyl)propanoateC14H21NO3[α]D25=-15.5 (c 1.4, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(S)
tert-Butyl (R)-3-amino-3-(2-methoxyphenyl)propanoateC14H21NO3[α]D25=+22.4 (c 2.4, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (R)-3-amino-3-(3,5-dimethoxyphenyl)propanoateC15H23NO4[α]D25=+12.3 (c 2.2, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (R)-3-amino-3-(3,4-dimethoxyphenyl)propanoateC15H23NO4[α]D25=+11.1 (c 2.5, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (R)-3-amino-3-(2,4-dimethoxyphenyl)propanoateC15H23NO4[α]D25=+17.0 (c 2.2, CHCl3)Source of chirality:asymmetric synthesisAbsolute configuration:(R)
tert-Butyl (R)-3-amino-3-phenylpropanoateC13H19NO2[α]D25=+18.3 (c 2.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
tert-Butyl (R)-3-amino-3-(4-biphenyl)propanoateC19H23NO2[α]D25=+11.8 (c 1.4, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
tert-Butyl (R)-3-amino-3-(piperon-3-yl)propanoateC14H19NO4[α]D25=+13.2 (c 2.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
tert-Butyl (R)-3-amino-3-(3-hydroxyphenyl)propanoateC13H19NO3[α]D25=+7.8 (c 1.2, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
tert-Butyl (R)-3-amino-3-(4-hydroxyphenyl)propanoateC13H19NO3[α]D25=+9.0 (c 1.1, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
tert-Butyl (S)-3-amino-3-(3,4-dihydroxyphenyl)propanoateC13H19NO4[α]D25=+8.9 (c 0.4, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-3-Aminobutanoic acidC4H9NO2[α]D25=-32.4 (c 0.6, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-Amino-5-methylhexanoic acidC7H15NO2[α]D25=-27.9 (c 0.7, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-3-Aminodecanoic acidC10H21NO2[α]D25=+2.5 (c 0.1, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-3-(4-methoxyphenyl)propanoic acidC10H13NO3[α]D25=-0.8 (c 0.2, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-3-(3-methoxyphenyl)propanoic acidC10H13NO3[α]D25=-3.9 (c 1.0, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-3-(3-methoxyphenyl)propanoic acidC10H13NO3[α]D25=+18.8 (c 0.6, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-3-Amino-3-(3,5-dimethoxyphenyl)propanoic acidC11H15NO4[α]D25=-0.8 (c 0.7, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-Amino-3-(3,4- dimethoxyphenyl)propanoic acidC11H15NO4[α]D25=-0.9 (c 0.7, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-3-Amino-3-(2,4-dimethoxyphenyl)propanoic acidC11H15NO4[α]D25=+5.3 (c 0.6, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-3-Amino-3-phenylpropanoic acidC9H11NO2[α]D25=+6.8 (c 0.9, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-Amino-3-(4-biphenyl)propanoic acid hydrochlorideC15H16NO2Cl[α]D25=-3.3 (c 0.8, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-3-Amino-3-(piperon-3-yl)propanoic acidC10H11NO4[α]D25=+42.4 (c 0.3, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(R)-3-Amino-3-(3-hydroxyphenyl)propanoic acidC9H11NO3[α]D25=+7.2 (c 0.5, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(R)-3-Amino-3-(4-hydroxyphenyl)propanoic acidC9H11NO3[α]D25=-6.0 (c 0.6, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (R)
(S)-3-Amino-3-(3,4-hydroxyphenyl)propanoic acid hydrochlorideC9H12NO4Cl[α]D25=+4.8 (c 0.2, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
