Regio- and Stereocontrol in Rhenium-Catalyzed Transposition of Allylic Alcohols

被引：77

作者：

Herrmann, Aaron T. ^{[1
]}

Saito, Tatsuo ^{[1
]}

Stivala, Craig E. ^{[1
]}

Tom, Janine ^{[1
]}

Zakarian, Armen ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 17期

基金：

日本学术振兴会;

关键词：

METAL OXO COMPLEXES; MOLYBDENUM COMPLEXES; SILYL ETHERS; ISOMERIZATION; 1,3-ISOMERIZATION;

D O I：

10.1021/ja101673v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A hydroxyl group-directed, highly regio- and stereoselective transposition of allylic alcohols based on rhenium catalysis has been developed. The method is suitable for a direct isomerization of acetals into the thermodynamically preferred isomer as long as one of the hydroxyl groups is allylic. This method will expand the scope of rhenium-catalyzed alcohol transpositions for complex molecule synthesis.

引用

页码：5962 / +

页数：3

共 20 条

[11] Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy
Gesinski, Michael R.
Tadpetch, Kwanruthai
Rychnovsky, Scott D.
[J]. ORGANIC LETTERS, 2009, 11 (22) : 5342 - 5345
[12] Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers
Hansen, Eric C.
Lee, Daesung
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) : 8142 - 8143
[13] SELECTIVE ALLYLIC REARRANGEMENT WITH TUNGSTEN CATALYST
HOSOGAI, T
FUJITA, Y
NINAGAWA, Y
NISHIDA, T
[J]. CHEMISTRY LETTERS, 1982, (03) : 357 - 360
[14] SUBSTRATE-DIRECTABLE CHEMICAL-REACTIONS
HOVEYDA, AH
EVANS, DA
FU, GC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1307 - 1370
[15] Approach to the synthesis of Cladiell-11-ene-3,6,7-triol
Hutchison, John M.
Lindsay, Harriet A.
Dormi, Silvana S.
Jones, Gavin D.
Vicic, David A.
McIntosh, Matthias C.
[J]. ORGANIC LETTERS, 2006, 8 (17) : 3663 - 3665
[16] 1,3-transposition of allylic alcohols catalyzed by methyltrioxorhenium
Jacob, J
Espenson, JH
Jensen, JH
Gordon, MS
[J]. ORGANOMETALLICS, 1998, 17 (09) : 1835 - 1840
[17] ISOMERIZATION OF ALLYLIC ALCOHOLS CATALYZED BY VANADIUM OR MOLYBDENUM COMPLEXES
MATSUBARA, S
OKAZOE, T
OSHIMA, K
TAKAI, K
NOZAKI, H
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (03) : 844 - 849
[18] Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis
Morrill, C
Grubbs, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2842 - 2843
[19] Rhenium-catalyzed 1,3-isomerization of allylic alcohols: Scope and chirality transfer
Morrill, Christie
Beutner, Gregory L.
Grubbs, Robert H.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) : 7813 - 7825
[20] Rhenium(VII) Catalysis of Prins Cyclization Reactions
Tadpetch, Kwanruthai
Rychnovsky, Scott D.
[J]. ORGANIC LETTERS, 2008, 10 (21) : 4839 - 4842

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