Literature DB >> 24281923

Iridium-catalyzed asymmetric ring-opening reactions of azabenzonorbornadiene with carboxylic acid nucleophiles.

Yuhua Long1, Wenling Wang, Dingqiao Yang, Han Jiang, Kaixuan Chen, Yali Fang.   

Abstract

Iridium-catalyzed asymmetric ring-opening reaction of N-substituted azabenzonorbornadienes with various carboxylic acids has been developed. The ring-opening reaction offered trans-1,2-dihydronaphthalene products containing an allylic carboxylate moiety in moderate yields (up to 89 %) with high enantioselectivities (up to 96 %). The trans-configuration of the products was confirmed by X-ray crystallography.

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Year:  2013        PMID： 24281923     DOI： 10.1007/s11030-013-9491-5

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  15 in total

1.  Copper-catalyzed anti-stereocontrolled ring opening of oxabicyclic alkenes with grignard reagents.

Authors:  Ramón Gómez Arrayás; Silvia Cabrera; Juan C Carretero
Journal:  Org Lett       Date:  2003-04-17       Impact factor: 6.005

2.  Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents.

Authors:  Pieter H Bos; Alena Rudolph; Manuel Pérez; Martín Fañanás-Mastral; Syuzanna R Harutyunyan; Ben L Feringa
Journal:  Chem Commun (Camb)       Date:  2012-01-03       Impact factor: 6.222

3.  Highly stereoselective ring-opening addition of terminal acetylenes to bicyclic olefins catalyzed by nickel complexes.

Authors:  Dinesh Kumar Rayabarapu; Chii-Feng Chiou; Chien-Hong Cheng
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

4.  Rhodium-catalyzed ring-opening reactions of N-boc-azabenzonorbornadienes with amine nucleophiles.

Authors:  Yong-hwan Cho; Valentin Zunic; Hisanori Senboku; Madeline Olsen; Mark Lautens
Journal:  J Am Chem Soc       Date:  2006-05-31       Impact factor: 15.419

5.  Copper-catalyzed anti-stereocontrolled ring-opening of azabicyclic alkenes with Grignard reagents.

Authors:  Ramón Gómez Arrayás; Silvia Cabrera; Juan C Carretero
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

6.  Ruthenium-catalyzed isomerization of oxa/azabicyclic alkenes: an expedient route for the synthesis of 1,2-naphthalene oxides and imines.

Authors:  Karine Villeneuve; William Tam
Journal:  J Am Chem Soc       Date:  2006-03-22       Impact factor: 15.419

7.  New catalytic reactions of oxa- and azabicyclic alkenes.

Authors:  Dinesh Kumar Rayabarapu; Chien-Hong Cheng
Journal:  Acc Chem Res       Date:  2007-06-26       Impact factor: 22.384

8.  Iridium-catalyzed asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with secondary amine nucleophiles.

Authors:  Dingqiao Yang; Yuhua Long; Huan Wang; Zhenming Zhang
Journal:  Org Lett       Date:  2008-10-04       Impact factor: 6.005

9.  Rhodium-catalyzed asymmetric ring-opening alkynylation of azabenzonorbornadienes.

Authors:  Takahiro Nishimura; Eiji Tsurumaki; Takahiro Kawamoto; Xun-Xiang Guo; Tamio Hayashi
Journal:  Org Lett       Date:  2008-08-19       Impact factor: 6.005

10.  Nickel-catalyzed addition of alkenylzirconium reagents to bicyclic olefins: a highly regio- and stereoselective ring-opening reaction.

Authors:  Ming-Si Wu; Dinesh Kumar Rayabarapu; Chien-Hong Cheng
Journal:  J Org Chem       Date:  2004-11-26       Impact factor: 4.354
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