| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345760 | Tetrahedron: Asymmetry | 2014 | 7 Pages |
The N-hydroxymethyl derivatives of α-amino aldehydes 1 were utilized for the effective synthesis of several β-amino-α-hydroxy acid derivatives in a one-pot process starting from the corresponding α-amino aldehydes. Properly protected methyl esters 3 were prepared in 65–79% yields from α-amino aldehyde derivatives 1 with more than 20:1 stereoselectivity. The application of suitably protected β-amino-α-hydroxy esters was shown by an efficient synthesis of the bioactive peptide, bestatin, and its more potent analogue, AHPBA-Val, in high yields from ent-3a.
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3-tert-Butyl 5-methyl (4S,5R)-4-benzyloxazolidine-3,5-dicarboxylateC17H23NO5[α]D13=-25.6 (c 0.76, CHCl3)Absolute configuration: (4S,5R)
3-tert-Butyl 5-methyl (4S,5R)-4-isobutyloxazoline-3,5-dicarboxylateC14H25NO5[α]D16=-6.7 (c 0.34, CHCl3)Absolute configuration: (4S,5R)
3-tert-Butyl 5-methyl (4S,5R)-4-isopropyloxazolidine-3,5-dicarboxylateC13H23NO5[α]D17=-10.7 (c 1.17, CHCl3)Absolute configuration: (4S,5R)
3-tert-Butyl 5-methyl (4S,5R)-4-methyloxazolidine-3,5-dicarboxylateC11H19NO5[α]D15=-5.9 (c 0.44, CHCl3)Absolute configuration: (4S,5R)
3-tert-Butyl 5-methyl (4S,5R)-4-((tert-butyldimethylsilyloxy)methyl)oxazolidine-3,5-dicarboxylateC17H33NO6Si[α]D15=-10.5 (c 0.71, CHCl3)Absolute configuration: (4S,5R)
tert-Butyl (4S,5R)-4-benzyl-5-(nitromethyl)oxazolidine-3-carboxylateC16H22N2O5[α]D15=-5.7 (c 2.53, CHCl3)Absolute configuration: (4S,5R)
tert-Butyl (4S,5R)-4-isobutyl-5-(nitromethyl)oxazolidine-3-carboxylateC13H24N2O5[α]D14=-8.2 (c 0.26, CHCl3)Absolute configuration: (4R,5S)
3-(tert-Butoxycarbonyl)-(4R,5S)-4-benzyloxazolidine-5-carboxylic acidC16H21NO5[α]D14=+17.0 (c 0.92, CHCl3)Absolute configuration: (4R,5S)
[3-(tert-Butoxycarbonyl)-(4R,5S)-4-benzyloxazolidine-5-carboxylic acid]-l-leucine methyl esterC23H34N2O6[α]D15=-10.7 (c 0.96, CHCl3)Absolute configuration: (4R,5S)
[3-(tert-Butoxycarbonyl)-(4R,5S)-4-benzyloxazolidine-5-carboxylic acid]-l-valine methyl esterC22H32N2O6[α]D15=-0.8 (c 0.54, CHCl3)Absolute configuration: (4R,5S)
