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Literature DB >> 20180519

Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.

Paramita Mukherjee¹, Ross A Widenhoefer.

Abstract

A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF(6) catalyzes the intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regioselectivity and syn-stereoselectivity.

Entities: Chemical Disease Species

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Year: 2010 PMID： 20180519 PMCID： PMC2929168 DOI： 10.1021/ol902923e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

25 in total

1. Water enables direct use of allyl alcohol for Tsuji-Trost reaction without activators.

Authors: Hidenori Kinoshita; Hiroshi Shinokubo; Koichiro Oshima
Journal: Org Lett Date: 2004-10-28 Impact factor: 6.005

2. Bismuth-catalyzed direct substitution of the hydroxy group in alcohols with sulfonamides, carbamates, and carboxamides.

Authors: Hongbo Qin; Noriyuki Yamagiwa; Shigeki Matsunaga; Masakatsu Shibasaki
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: sulfamic acid as ammonia equivalent.

Authors: Christian Defieber; Martin A Ariger; Patricia Moriel; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Enantioselective gold-catalyzed allylic alkylation of indoles with alcohols: an efficient route to functionalized tetrahydrocarbazoles.

Authors: Marco Bandini; Astrid Eichholzer
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

5. Synthesis and structural characterisation of stable cationic gold(I) alkene complexes.

Authors: Thomas N Hooper; Michael Green; John E McGrady; Jaynika R Patel; Christopher A Russell
Journal: Chem Commun (Camb) Date: 2009-06-05 Impact factor: 6.222

6. An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.

Authors: Aaron Aponick; Chuan-Ying Li; Jeremy Malinge; Emerson Finco Marques
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

7. (Pi-allyl)palladium complexes bearing diphosphinidenecyclobutene ligands (DPCB): highly active catalysts for direct conversion of allylic alcohols.

Authors: Fumiyuki Ozawa; Hideyuki Okamoto; Seiji Kawagishi; Shogo Yamamoto; Tatsuya Minami; Masaaki Yoshifuji
Journal: J Am Chem Soc Date: 2002-09-18 Impact factor: 15.419

8. Ion pairing in cationic olefin-gold(I) complexes.

Authors: Daniele Zuccaccia; Leonardo Belpassi; Francesco Tarantelli; Alceo Macchioni
Journal: J Am Chem Soc Date: 2009-03-11 Impact factor: 15.419

9. Platinum-catalyzed direct amination of allylic alcohols under mild conditions: ligand and microwave effects, substrate scope, and mechanistic study.

Authors: Takashi Ohshima; Yoshiki Miyamoto; Junji Ipposhi; Yasuhito Nakahara; Masaru Utsunomiya; Kazushi Mashima
Journal: J Am Chem Soc Date: 2009-10-14 Impact factor: 15.419

10. Intermolecular hydroamination of ethylene and 1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes.

Authors: Zhibin Zhang; Seong Du Lee; Ross A Widenhoefer
Journal: J Am Chem Soc Date: 2009-04-22 Impact factor: 15.419

14 in total

1. Gold(I)-catalyzed enantioselective intramolecular dehydrative amination of allylic alcohols with carbamates.

Authors: Paramita Mukherjee; Ross A Widenhoefer
Journal: Angew Chem Int Ed Engl Date: 2012-01-03 Impact factor: 15.336

2. Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

Authors: Paramita Mukherjee; Ross A Widenhoefer
Journal: Org Lett Date: 2011-02-11 Impact factor: 6.005

3. Regio- and enantioselective hydroamination of dienes by gold(I)/menthol cooperative catalysis.

Authors: Osamu Kanno; Wataru Kuriyama; Z Jane Wang; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2011-09-07 Impact factor: 15.336

4. The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex.

Authors: Paramita Mukherjee; Ross A Widenhoefer
Journal: Chemistry Date: 2013-01-24 Impact factor: 5.236

5. A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers.

Authors: Berenger Biannic; Thomas Ghebreghiorgis; Aaron Aponick
Journal: Beilstein J Org Chem Date: 2011-06-14 Impact factor: 2.883

6. Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Authors: He Huang; Yu Zhou; Hong Liu
Journal: Beilstein J Org Chem Date: 2011-07-04 Impact factor: 2.883

7. Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols.

Authors: Michel Chiarucci; Mirko Locritani; Gianpiero Cera; Marco Bandini
Journal: Beilstein J Org Chem Date: 2011-09-01 Impact factor: 2.883

8. Gold(I)-catalysed one-pot synthesis of chromans using allylic alcohols and phenols.

Authors: Eloi Coutant; Paul C Young; Graeme Barker; Ai-Lan Lee
Journal: Beilstein J Org Chem Date: 2013-09-04 Impact factor: 2.883

9. Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study.

Authors: Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal: Chemistry Date: 2015-08-06 Impact factor: 5.236

10. Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.

Authors: Lorena Herkert; Samantha L J Green; Graeme Barker; David G Johnson; Paul C Young; Stuart A Macgregor; Ai-Lan Lee
Journal: Chemistry Date: 2014-07-30 Impact factor: 5.236