Unusual reaction of azetidine-2,3-diones with primary amines.: Straightforward asymmetric synthesis of α-amino acid and peptide derivatives

被引：22

作者：

Alcaide, B ^{[1
]}

Almendros, P ^{[1
]}

Aragoncillo, C ^{[1
]}

机构：

[1] Univ Complutense, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 09期

关键词：

D O I：

10.1039/a909688d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented one-step synthesis of unnatural alpha-amino acid and peptide derivatives, in both the racemic and optically pure forms, using azetidine-2,3-diones as building blocks has been developed by treatment with primary amines.

引用

页码：757 / 758

页数：2

共 31 条

[11] SYNTHESIS OF 6-VINYLIDENEPENAMS
BUYNAK, JD
BORATE, HB
LAMB, GW
KHASNIS, DD
HUSTING, C
ISOM, H
SIRIWARDANE, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) : 1325 - 1335
[12] Indium and zinc mediated Barbier type reactions: Allylation and propargylation reactions of 6-oxopenicillanate and 7-oxocephalosporanate
Cho, YS
Lee, JE
Pae, AN
Choi, KI
Koh, HY
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1725 - 1728
[13] Coppola G.M., 1987, ASYMMETRIC SYNTHESIS
[14] REAGENTS AND SYNTHETIC METHODS .69. SYNTHETIC UTILITY OF AZETIDINE-2,3-DIONES - A NEW APPROACH TO 3-HYDROXYETHYL-BETA-LACTAMS AND ALPHA-AMINO-ACID DERIVATIVES
COSSIO, FP
LOPEZ, C
OIARBIDE, M
PALOMO, C
APARICIO, D
RUBIALES, G
[J]. TETRAHEDRON LETTERS, 1988, 29 (25) : 3133 - 3136
[15] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
DUTHALER, RO
[J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
[16] USE OF PI-ALLYLTRICARBONYLIRON LACTAM COMPLEXES IN THE PREPARATION OF NOCARDICIN DERIVATIVES - SYNTHESIS OF (-)-3-OXO-1-[(PARA-BENZYLOXYPHENYL)-BENZYLOXYCARBONYLMETHYL]AZETIDIN-2-ONE
HODGSON, ST
HOLLINSHEAD, DM
LEY, SV
LOW, CMR
WILLIAMS, DJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2375 - 2381
[17] Studies on lactams .102. Environ-friendly approaches to densely functionalized beta-lactams
Jayaraman, M
Manhas, MS
Bose, AK
[J]. TETRAHEDRON LETTERS, 1997, 38 (05) : 709 - 712
[18] NANGIA A, 1995, CURR SCI INDIA, V68, P699
[19] NICOTINIC RECEPTOR-BINDING SITE PROBED WITH UNNATURAL AMINO-ACID-INCORPORATION IN INTACT-CELLS
NOWAK, MW
KEARNEY, PC
SAMPSON, JR
SAKS, ME
LABARCA, CG
SILVERMAN, SK
ZHONG, W
THORSON, JS
ABELSON, JN
DAVIDSON, N
SCHULTZ, PG
DOUGHERTY, DA
LESTER, HA
[J]. SCIENCE, 1995, 268 (5209) : 439 - 442
[20] Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the beta-lactam synthon method
Ojima, I
Delaloge, F
[J]. CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) : 377 - 386

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