Preparation and evaluation of a cyclic acyl nitrone as a synthon for stereospecific α-amino acid synthesis

被引：29

作者：

Baldwin, SW ^{[1
]}

Young, BG ^{[1
]}

McPhail, AT ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 38期

关键词：

nitrones; cycloadditions; stereoselection; X-ray crystal structures;

D O I：

10.1016/S0040-4039(98)01474-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation and characterization of cyclic optically active (5R)-3,4,5,6-tetrahydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide (2) is described. This nitrone, which is viewed as a template for the synthesis of gamma-oxygenated alpha-amino acids, reacts with alkenes efficiently and with high stereospecificity. (C) 1998 Elsevier Science Ltd. AII rights reserved.

引用

页码：6819 / 6822

页数：4

共 9 条

[1] [Anonymous], 1992, ALDRICHIM ACTA
[2] DEVELOPMENT OF CHIRAL STABILIZED AZOMETHINE YLIDES - A CHIRAL MEMORY RELAY SYSTEM
ANSLOW, AS
HARWOOD, LM
PHILLIPS, H
WATKIN, D
WONG, LF
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1343 - 1358
[3] Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis
[4] EPOXIDATION OF ALKENES BY DIOXIRANE INTERMEDIATES GENERATED IN THE REACTION OF POTASSIUM CAROATE WITH KETONES
CURCI, R
FIORENTINO, M
TROISI, L
EDWARDS, JO
PATER, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) : 4758 - 4760
[5] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON
DELLARIA, JF
SANTARSIERO, BD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) : 3916 - 3926
[6] Padwa A., 1991, Comprehensive Organic Synthesis, P1069, DOI DOI 10.1016/B978-0-08-052349-1.00116-5
[7] TUFARIELLO J, 1975, SYNTHESIS-STUTTGART, P205
[8] THE STEREOCHEMISTRY OF NITRONE-DIENE CYCLOADDITIONS - SYNTHESIS OF THE ALKALOIDS OF DARLINGIA-DARLINGIANA
TUFARIELLO, JJ
PUGLIS, JM
[J]. TETRAHEDRON LETTERS, 1986, 27 (11) : 1265 - 1268
[9] PRACTICAL ASYMMETRIC SYNTHESES OF ALPHA-AMINO-ACIDS THROUGH CARBON CARBON BOND CONSTRUCTIONS ON ELECTROPHILIC GLYCINE TEMPLATES
WILLIAMS, RM
SINCLAIR, PJ
ZHAI, D
CHEN, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) : 1547 - 1557

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