Literature DB >> 11950350

Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids.

Mark Lautens1, Chris Dockendorff, Keith Fagnou, Adrianna Malicki.   

Abstract

The first rhodium(I)-catalyzed asymmetric addition of organoboronic acids to oxabicyclic alkenes is reported. This asymmetric ring-opening (ARO) reaction can proceed in high yield under very mild conditions with electronically diverse organoboronic acids, in a highly diastereoselective and enantioselective manner. [structure: see text]

Entities:  

Year:  2002        PMID： 11950350     DOI： 10.1021/ol0256062

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


  11 in total

1.  Reactivity and selectivity in hydrovinylation of strained alkenes.

Authors:  Wang Liu; T V RajanBabu
Journal:  J Org Chem       Date:  2010-10-21       Impact factor: 4.354

2.  Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

3.  A homogeneous, recyclable polymer support for Rh(I)-catalyzed C-C bond formation.

Authors:  Ranjan Jana; Jon A Tunge
Journal:  J Org Chem       Date:  2011-09-23       Impact factor: 4.354

4.  Iridium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes with secondary amine nucleophiles.

Authors:  Dingqiao Yang; Ping Hu; Yuhua Long; Yujuan Wu; Heping Zeng; Hui Wang; Xiongjun Zuo
Journal:  Beilstein J Org Chem       Date:  2009-10-09       Impact factor: 2.883

5.  Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

6.  Rhodium-catalyzed asymmetric ring opening reactions of oxabicyclic alkenes: catalyst and substrate studies leading to a mechanistic working model.

Authors:  Mark Lautens; Keith Fagnou
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-05       Impact factor: 11.205

7.  Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: inversion of absolute configuration.

Authors:  P Andrew Evans; Daisuke Uraguchi
Journal:  J Am Chem Soc       Date:  2003-06-18       Impact factor: 15.419

8.  A homogeneous, recyclable rhodium(I) catalyst for the hydroarylation of Michael acceptors.

Authors:  Ranjan Jana; Jon A Tunge
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to alpha,beta-unsaturated ketones.

Authors:  Norihito Tokunaga; Kazuhiro Yoshida; Tamio Hayashi
Journal:  Proc Natl Acad Sci U S A       Date:  2004-02-23       Impact factor: 11.205

10.  Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Authors:  Harathi D Srinivas; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005
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