A FACILE CLAISEN REARRANGEMENT INVOLVING THE TRANSIENT TAUTOMERIC ENAMINE FORMS OF ALPHA-ALLYLOXYIMINES AND ALPHA-PROPARGYLOXYIMINES

被引：14

作者：

DESMAELE, D

CHAMPION, N

机构：

[1] Laboratoire de Chimie Organique, Faculte ́de Pharmacie., 92296 Chaa ̂tenay-Malabry, 5, rue J.B.Cle ́ment

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 31期

关键词：

IMINE-ENAMINE TAUTOMERISM; ACCELERATED CLAISEN REARRANGEMENT; 1,3] SIGMATROPIC SHIFT; ALPHA-AMINOKETONES;

D O I：

10.1016/S0040-4039(00)60106-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alpha-allyloxyimines rearrange smoothly to 2-amino-2-allyl-ketones by heating at 80-degrees-C for few hours, by Claisen rearrangement of the tautomeric secondary enamine. Similarly alpha-propargyloxyimine gave 2-amino-2-allenyl-ketones. By contrast, 2-benzyloxyimines afford rearranged 2-amino-2-benzyloxycyclopentanone by [1,3] sigmatropic shift.

引用

页码：4447 / 4450

页数：4

共 17 条

[1] SYNTHESIS OF SUBSTITUTED 2-AMINOPENT-4-ENALS AND 2-AMINO-3-(2-FURYL)PROPANALS VIA [3,3]-SIGMATROPIC AND [1,3]-SIGMATROPIC SHIFTS OF BETA-ALLYLOXYENAMINES
BARLUENGA, J
AZNAR, F
LIZ, R
BAYOD, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (21) : 1427 - 1428
[2] SUBSTITUENT EFFECTS ON THE ALIPHATIC CLAISEN REARRANGEMENT .1. SYNTHESIS AND REARRANGEMENT OF CYANO-SUBSTITUTED ALLYL VINYL ETHERS
BURROWS, CJ
CARPENTER, BK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) : 6983 - 6984
[3] SUBSTITUENT EFFECTS ON THE ALIPHATIC CLAISEN REARRANGEMENT .2. THEORETICAL-ANALYSIS
BURROWS, CJ
CARPENTER, BK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) : 6984 - 6986
[4] SYNTHESIS AND CLAISEN REARRANGEMENT OF ALKOXYALLYL ENOL ETHERS - EVIDENCE FOR A DIPOLAR TRANSITION-STATE
COATES, RM
ROGERS, BD
HOBBS, SJ
PECK, DR
CURRAN, DP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1160 - 1170
[5] THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES
DANGELO, J
DESMAELE, D
DUMAS, F
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 459 - 505
[6] ENANTIOSELECTIVE SYNTHESIS OF OXA-SPIRO COMPOUNDS
DESMAELE, D
DANGELO, J
[J]. TETRAHEDRON LETTERS, 1989, 30 (03) : 345 - 348
[7] A KINETIC STUDY OF THE ORTHO-CLAISEN REARRANGEMENT
GOERING, HL
JACOBSON, RR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (13) : 3277 - 3285
[8] PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS
GRIFFITH, WP
LEY, SV
WHITCOMBE, GP
WHITE, AD
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) : 1625 - 1627
[9] ANIONIC OXY-CLAISEN REARRANGEMENT OF ENOLATES OF ALPHA-ALLYLOXY KETONES - A REMARKABLE RATE-ACCELERATING EFFECT EXHIBITED BY THE NATURE OF THE COUNTERION
KOREEDA, M
LUENGO, JI
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) : 5572 - 5573
[10] OXYGEN-ATOM TRANSFER FROM IODOSOBENZENE TO KETENES, ALPHA-KETO CARBOXYLIC-ACIDS, AND KETONES
MORIARTY, RM
GUPTA, SC
HU, H
BERENSCHOT, DR
WHITE, KB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 686 - 688

← 1 2 →