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 50 条

[31] RHENIUM-CATALYZED PEROXIDATIONS
ESPENSON, JH
VASSELL, K
ABUOMAR, M
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 13 - INOR
[32] Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Trisubstituted Allylic Electrophiles
Chen, Ming
Hartwig, John F.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (38) : 11651 - 11655
[33] Palladium-Mediated Highly Regio- and Stereoselective Intermolecular β-Arylation on Allylic Alcohols: Synthesis of Functionalized Allylic Alcohols
Krishna, J.
Reddy, A. Gopi Krishna
Ramulu, B. Venkat
Mahendar, L.
Satyanarayana, G.
SYNLETT, 2012, (03) : 375 - 380
[34] Cobalt-Catalyzed Regio- and Enantioselective Allylic Alkylation of Malononitriles
Ghorai, Samir
Rehman, Sajid Ur
Xu, Wen-Bin
Huang, Wen-Yu
Li, Changkun
ORGANIC LETTERS, 2020, 22 (09) : 3519 - 3523
[35] Ir-catalyzed regio- and enantioselective decarboxylative allylic Alkylations
He, Hu
Zheng, Xiao-Jian
Li, Yi
Dai, Li-Xin
You, Shu-Li
ORGANIC LETTERS, 2007, 9 (21) : 4339 - 4341
[36] Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols
Zhang, Zhibin
Widenhoefer, Ross A.
ORGANIC LETTERS, 2008, 10 (10) : 2079 - 2081
[37] Palladium clay catalyzed regio- and stereospecific synthesis of beta,gamma-unsaturated acids by the carbonylation of allylic alcohols
Naigre, R
Alper, H
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 111 (1-2) : 11 - 15
[38] Regio- and stereoselective syntheses of piperidine derivatives via ruthenium-catalyzed coupling of propargylic amides and allylic alcohols
Murugesan, Sathiyamoorthy
Jiang, Fan
Achard, Mathieu
Bruneau, Christian
Derien, Sylvie
CHEMICAL COMMUNICATIONS, 2012, 48 (52) : 6589 - 6591
[39] Rhenium-Catalyzed Regio- and Stereoselective Synthesis of γ-Thio-α,β-unsaturated Ketones via Insertion of Terminal Alkynes into the C-S Bond
Nishi, Mitsumi
Kuninobu, Yoichiro
Takai, Kazuhiko
ORGANIC LETTERS, 2012, 14 (23) : 6116 - 6118
[40] Regio- and Enantioselective Pd-Catalyzed Allylic Amination of Monosubstituted Allylic Substrates with BocNHOMe
Zheng, Bao-Hui
Ding, Chang-Hua
Hou, Xue-Long
SYNLETT, 2011, (15) : 2262 - 2264

← 1 2 3 4 5 →