Highly selective methanesulfonic acid-catalyzed 1,3-isomerization of allylic alcohols

被引：32

作者：

Leleti, Rajender Reddy ^{[1
]}

Bin Hu ^{[1
]}

Prashad, Mahavir ^{[1
]}

Repic, Jan ^{[1
]}

机构：

[1] Novartis Pharmaceut Corp, Chem & Analyt Dev, Process R&D, E Hanover, NJ 07936 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 48期

关键词：

methanesulfonic acid; allylic alcohols; 1,3-isomerization; THF; water;

D O I：

10.1016/j.tetlet.2007.09.156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Secondary and tertiary allylic alcohols undergo 1,3-isomerization smoothly in the presence of methanesulfonic acid under simple and efficient conditions to afford selectively the corresponding primary E-allylic alcohols in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8505 / 8507

页数：3

共 17 条

[1]

CHARETTE AB, 1995, SYNLETT, P1197

[2]

FRANK RF, 2002, INORG CHEM COMMUN, V5, P384

[3]

GE W, 2005, INORG CHEM ACTA, V358, P933

[4]

Hill R.K., 1991, Comprehensive Organic Synthesis, V5, P785

[5] 1,3-transposition of allylic alcohols catalyzed by methyltrioxorhenium [J].

Jacob, J ;

Espenson, JH ;

Jensen, JH ;

Gordon, MS .

ORGANOMETALLICS, 1998, 17 (09) :1835-1840

[6]

Katsuki T., 1999, COMPREHENSIVE ASYMME, V2, P621

[7] Synthesis and reactions of allylic, allenic, vinylic, and arylmetal reagents from halides and esters via transient organopalladium intermediates [J].

Marshall, JA .

CHEMICAL REVIEWS, 2000, 100 (08) :3163-3185

[8]

MILTON LH, 1990, J MED CHEM, V33, P908

[9] Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis [J].

Morrill, C ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2842-2843

[10] Rhenium-catalyzed 1,3-isomerization of allylic alcohols: Scope and chirality transfer [J].

Morrill, Christie ;

Beutner, Gregory L. ;

Grubbs, Robert H. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7813-7825

← 1 2 →