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

被引：30
|
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
收藏
页码：8505 / 8507
页数：3
相关论文
共 50 条
  • [21] ACID-CATALYZED ISOMERIZATION AND DEHYDRATION OF GLYCERALDEHYDE AND 1,3-DIHYDROXY-2-PROPANONE
    LOOKHART, GL
    FEATHER, MS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1975, 170 (AUG24): : 7 - 7
  • [22] 1,3-transposition of allylic alcohols catalyzed by methyltrioxorhenium
    Jacob, J
    Espenson, JH
    Jensen, JH
    Gordon, MS
    ORGANOMETALLICS, 1998, 17 (09) : 1835 - 1840
  • [23] ACID-CATALYZED ISOMERIZATION OF DIALKYLBENZENES
    CSICSERY, SM
    JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (11): : 3338 - &
  • [24] AN ACID-CATALYZED ISOMERIZATION OF ISOATISINE
    DESAI, HK
    JIANG, QP
    PELLETIER, SW
    JOURNAL OF NATURAL PRODUCTS, 1990, 53 (05): : 1374 - 1378
  • [25] ACID-CATALYZED ISOMERIZATION OF TRICYCLICS
    BUSHICK, RD
    JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11): : 4085 - &
  • [26] Highly enantioselective isomerization of primary allylic alcohols catalyzed by (P,N)-iridium complexes
    Mantilli, Luca
    Gerard, David
    Torche, Sonya
    Besnard, Celine
    Mazet, Clement
    PURE AND APPLIED CHEMISTRY, 2010, 82 (07) : 1461 - 1469
  • [27] ACID-CATALYZED ISOMERIZATION OF THUJOPSENE
    DAENIKER, HU
    KAISER, K
    HOCHSTET.AR
    KITCHENS, GC
    JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (01): : 1 - &
  • [28] Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO
    Vatele, Jean-Michel
    TETRAHEDRON, 2010, 66 (04) : 904 - 912
  • [29] Direct palladium/carboxylic acid-catalyzed allylation of anilines with allylic alcohols in water
    Yang, SC
    Hsu, YC
    Gan, KH
    TETRAHEDRON, 2006, 62 (17) : 3949 - 3958
  • [30] ON THE 1,3-ISOMERIZATION OF NONRACEMIC ALPHA-(ALKOXY)ALLYLSTANNANES
    MARSHALL, JA
    GUNG, WY
    TETRAHEDRON LETTERS, 1989, 30 (52) : 7349 - 7352
12345