Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids.: Applications in Wittig reactions and heterocycle synthesis

被引：54

作者：

Davies, SB ^{[1
]}

McKervey, MA ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 06期

关键词：

D O I：

10.1016/S0040-4039(98)02573-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Z-gamma-amino alcohols derived from nonracemic beta-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：1229 / 1232

页数：4

共 18 条

[1] Dess-Martin periodinane oxidation of alcohols in the presence of stabilized phosphorus ylides: A convenient method for the homologation of alcohols via unstable aldehydes
Barrett, AGM
Hamprecht, D
Ohkubo, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) : 9376 - 9378
[2] CERVINKA O, 1965, COLLECT CZECH CHEM C, V30, P1742
[3] SYNTHETIC APPROACHES TOWARDS MANZAMINE - AN EASY PREPARATION OF BETA-AMINO ALDEHYDES
CHESNEY, A
MARKO, IE
[J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (20) : 3167 - 3180
[4] CHESNEY A, 1992, SYNLETT, P275
[5] OXIDATION OF ALPHA-DIAZOKETONES DERIVED FROM L-AMINO-ACIDS AND DIPEPTIDES USING DIMETHYLDIOXIRANE - SYNTHESIS AND REACTIONS OF HOMOCHIRAL N-PROTECTED ALPHA-AMINO GLYOXALS
DARKINS, P
MCCARTHY, N
MCKERVEY, MA
YE, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) : 1222 - 1223
[6] DAVIES SG, 1995, SYNLETT, P700
[7] Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines:: (+)-dihydropinidine
Davis, FA
Szewczyk, JM
[J]. TETRAHEDRON LETTERS, 1998, 39 (33) : 5951 - 5954
[8] DOYLE MP, 1997, MODERN CATALYTIC MET, P487
[9] ENDERS D, 1993, LIEBIGS ANN CHEM, P173
[10] STEREOSELECTIVE ADDITIONS OF CHIRAL ALPHA-SULFINYL KETIMINE ANIONS TO ENE ESTERS - ASYMMETRIC SYNTHESES OF INDOLO[2,3-A]QUINOLIZIDINE AND YOHIMBAN ALKALOIDS
HUA, DH
BHARATHI, SN
PANANGADAN, JAK
TSUJIMOTO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) : 6998 - 7007

← 1 2 →