Concise enantio- and diastereoselective synthesis of α-hydroxy-α-methyl-β-amino acids

被引：37

作者：

Roers, R ^{[1
]}

Verdine, GL ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 21期

关键词：

catalytic aldol; Curtius rearrangement; beta-amino acid;

D O I：

10.1016/S0040-4039(01)00457-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported here is an efficient procedure for enantio- and diastereoselective synthesis of purr beta -amino acids that display a tert-hydroxyl functionality in the alpha -position. Key steps include a catalytic asymmetric aldol reaction and a modified Curtius rearrangement to form oxazolidinone intermediates, which are chemoselectively opened to furnish N-protected alpha -hydroxy-alpha -methyl-beta -amino acids. A modified work-up procedure of the: aldol reaction allows for recovery of up to 90% of bisoxazolinyl ligands from the catalysts. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3563 / 3565

页数：3

共 17 条

[1] AMASTATIN, AN INHIBITOR OF AMINOPEPTIDASE-A, PRODUCED BY ACTINOMYCETES
AOYAGI, T
TOBE, H
KOJIMA, F
HAMADA, M
TAKEUCHI, T
UMEZAWA, H
[J]. JOURNAL OF ANTIBIOTICS, 1978, 31 (06) : 636 - 638
[2] Concise synthesis of conformationally constrained pybox ligands
Davies, IW
Gerena, L
Lu, N
Larsen, RD
Reider, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9629 - 9630
[3] C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
Evans, DA
MacMillan, DWC
Campos, KR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) : 10859 - 10860
[4] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
Evans, DA
Burgey, CS
Kozlowski, MC
Tregay, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 686 - 699
[5] An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes
Evans, DA
Peterson, GS
Johnson, JS
Barnes, DM
Campos, KR
Woerpel, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) : 4541 - 4544
[6] LEWIS ACID MEDIATED ALDOL CONDENSATIONS USING THIOESTER SILYL KETENE ACETALS
GENNARI, C
BERETTA, MG
BERNARDI, A
MORO, G
SCOLASTICO, C
TODESCHINI, R
[J]. TETRAHEDRON, 1986, 42 (03) : 893 - 909
[7] Chiral bis(oxazoline) copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions
Johnson, JS
Evans, DA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 325 - 335
[8] Juaristi E., 1997, ENANTIOSELECTIVE SYN
[9] Diastereoselective addition of grignard reagents to azetidine-2,3-dione: Synthesis of novel Taxol(R) analogues
Kant, J
Schwartz, WS
Fairchild, C
Gao, Q
Huang, S
Long, BH
Kadow, JF
Langley, DR
Farina, V
Vyas, D
[J]. TETRAHEDRON LETTERS, 1996, 37 (36) : 6495 - 6498
[10] APPLICATION OF YEAST-CATALYZED REDUCTIONS TO SYNTHESIS OF (2R,3S)-PHENYLISOSERINE
KEARNS, J
KAYSER, MM
[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2845 - 2848

← 1 2 →