An unusual rearrangement of N,N-dibenzyl-2-aminopropanal to N,N-dibenzyl-1-aminopropanone.

被引：7

作者：

Adia, M ^{[1
]}

Henaff, N ^{[1
]}

Whiting, A ^{[1
]}

机构：

[1] UMIST,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(97)00555-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-dibenzyl-2-aminopropanal la derived from alanine rearranges to the corresponding ketone, N,N-dibenzyl-1-aminopropanone upon exposure to either silica gel or pyridinium acetate. Similar rearrangements do not occur with aldehydes derived from phenylalinine, valine, leucine, proline or phenylglycine. One mechanistic explanation for the rearrangement is a facile 1,2-methyl shift, followed by 12-hydrogen shift. (C) 1997 Elsevier Science Ltd.

引用

页码：3101 / 3102

页数：2

共 12 条

[1] ADIA M, UNPUB
[2] Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors
Beaulieu, PL
Wernic, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3635 - 3645
[3] DUHAMEL L, 1970, B SOC CHIM FR, P1797
[4] A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES
EVANS, BE
RITTLE, KE
HOMNICK, CF
SPRINGER, JP
HIRSHFIELD, J
VEBER, DF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4615 - 4625
[5] ITO A, 1975, CHEM PHARM BULL, V23, P3081
[6] KIRRMANN A, 1966, B SOC CHIM FR, P1732
[7] MACKAY SP, 1993, Z NATURFORSCH C, V48, P782
[8] STEREOSELECTIVE SYNTHESIS OF BETA-AMINO ALCOHOLS FROM OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS
REETZ, MT
DREWES, MW
SCHMITZ, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11): : 1141 - 1143
[9] NEW APPROACHES TO THE USE OF AMINO-ACIDS AS CHIRAL BUILDING-BLOCKS IN ORGANIC-SYNTHESIS
REETZ, MT
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12): : 1531 - 1546
[10] SYNTHESIS OF (3S,4S)-4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID-DERIVATIVES - ANALYSIS OF DIASTEREOMERIC PURITY
RICH, DH
SUN, ET
BOPARAI, AS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) : 3624 - 3626

← 1 2 →