Regioselective nucleophilic ring opening reactions of 2,2-disubstituted aziridines - The asymmetric synthesis of alpha,alpha-disubstituted amino acids

被引：42

作者：

Burgaud, BGM ^{[1
]}

Horwell, DC ^{[1
]}

Padova, A ^{[1
]}

Pritchard, MC ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,PARKE DAVIS NEUROSCI RES CTR,CAMBRIDGE CB2 2QB,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 40期

关键词：

D O I：

10.1016/0040-4020(96)00784-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper a broadly applicable synthesis of chiral alpha,alpha-disubstituted amino acids is outlined based upon regioselective ring opening of aziridine derivatives. Examples of nitrogen, sulphur and carbon nucleophiles were found to preferentially attack the C3 position of chiral 2-methyl-2-silyloxymethyl aziridines to provide a range of alpha,alpha-disubstituted amino acid derivatives in good yield. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：13035 / 13050

页数：16

共 21 条

[1] AMINO-ACID SYNTHESIS VIA RING-OPENING OF N-SULFONYL AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
SPIVEY, AC
SCHOFIELD, CJ
SWEENEY, JB
[J]. TETRAHEDRON, 1993, 49 (28) : 6309 - 6330
[2] Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for alpha-amino acid synthesis
Baldwin, JE
Farthing, CN
Russell, AT
Schofield, CJ
Spivey, AC
[J]. TETRAHEDRON LETTERS, 1996, 37 (21) : 3761 - 3764
[3] THE DEVELOPMENT OF A NOVEL SERIES OF NONPEPTIDE TACHYKININ NK3 RECEPTOR-SELECTIVE ANTAGONISTS
BODEN, P
EDEN, JM
HODGSON, J
HORWELL, DC
PRITCHARD, MC
RAPHY, J
SUMANCHAUHAN, N
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) : 1773 - 1778
[4] THE ASYMMETRIC-SYNTHESIS OF NONPEPTIDE CCK-A RECEPTOR AGONISTS
BURGAUD, BGM
HORWELL, DC
PRITCHARD, MC
BERNAD, N
MARTINEZ, J
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (05) : 1081 - 1084
[5] SYNTHESIS OF ALPHA-AMINO-ACIDS BY RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH CARBON NUCLEOPHILES
CHURCH, NJ
YOUNG, DW
[J]. TETRAHEDRON LETTERS, 1995, 36 (01) : 151 - 154
[6] REACTIVITY OF 2,3-AZIRIDINO-2,3-DIDEOXY-D-LYXONO-GAMMA-LACTONE DERIVATIVES, RIGID ANALOGS OF AZIRIDINE-2-CARBOXYLIC ESTERS, TOWARD SOFT AND HARD NUCLEOPHILES - CONTROL OF LACTONE VS AZIRIDINE RING-OPENING AND C-2 VS C-3 REGIOSELECTIVITY
DAUBAN, P
DUBOIS, L
DAU, METH
DODD, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) : 2035 - 2043
[7] 3-AMINO-2H-AZIRINES - SYNTHONS FOR ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS IN HETEROCYCLE AND PEPTIDE-SYNTHESIS
HEIMGARTNER, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (03) : 238 - 264
[8] RATIONALLY DESIGNED DIPEPTOID ANALOGS OF CCK - A FREE WILSON FUJITA BAN ANALYSIS OF SOME ALPHA-METHYLTRYPTOPHAN DERIVATIVES AS CCK-B ANTAGONISTS
HIGGINBOTTOM, M
KNEEN, C
RATCLIFFE, GS
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (09) : 1572 - 1577
[9] 'Targeted' molecular diversity: Design and development of non-peptide antagonists for cholecystokinin and tachykinin receptors
Horwell, D
Pritchard, M
Raphy, J
Ratcliffe, G
[J]. IMMUNOPHARMACOLOGY, 1996, 33 (1-3): : 68 - 72
[10] RATIONALLY DESIGNED DIPEPTOID ANALOGS OF CCK - ALPHA-METHYLTRYPTOPHAN DERIVATIVES AS HIGHLY SELECTIVE AND ORALLY ACTIVE GASTRIN AND CCK-B ANTAGONISTS WITH POTENT ANXIOLYTIC PROPERTIES
HORWELL, DC
HUGHES, J
HUNTER, JC
PRITCHARD, MC
RICHARDSON, RS
ROBERTS, E
WOODRUFF, GN
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) : 404 - 414

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