Literature DB >> 25233924

Rhodium-catalyzed arylative cyclization for the enantioselective synthesis of (trifluoromethyl)cyclobutanols.

Thomas Johnson1, Ken-Loon Choo, Mark Lautens.   

Abstract

A rhodium-catalyzed cyclization of 1-(trifluoromethyl)-4-alkyn-1-ones with arylboronic acids is described to yield a novel class of small rings: (trifluoromethyl)cyclobutanols bearing an exocyclic double bond. The use of a rhodium/chiral diene complex allowed the reaction to proceed under mild conditions, often with high enantioselectivity. An X-ray crystal structure was obtained confirming the formation of the four-membered ring products.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; cyclobutanes; diene ligands; fluorine; rhodium

Year:  2014        PMID: 25233924     DOI: 10.1002/chem.201404896

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  6 in total

1.  A Mixed-Ligand Chiral Rhodium(II) Catalyst Enables the Enantioselective Total Synthesis of Piperarborenine B.

Authors:  Robert A Panish; Srinivasa R Chintala; Joseph M Fox
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-16       Impact factor: 15.336

2.  Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration.

Authors:  Alistair Groves; Jinwei Sun; Hal R I Parke; Michael Callingham; Stephen P Argent; Laurence J Taylor; Hon Wai Lam
Journal:  Chem Sci       Date:  2020-02-06       Impact factor: 9.825

3.  Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.

Authors:  Benjamin M Partridge; Michael Callingham; William Lewis; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-19       Impact factor: 15.336

4.  Synthesis of bridged tricyclo[5.2.1.01,5]decanes via nickel-catalyzed asymmetric domino cyclization of enynones.

Authors:  Jiachang Chen; Yiming Wang; Zhengtian Ding; Wangqing Kong
Journal:  Nat Commun       Date:  2020-04-20       Impact factor: 14.919

5.  Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization.

Authors:  Christopher Clarke; Celia A Incerti-Pradillos; Hon Wai Lam
Journal:  J Am Chem Soc       Date:  2016-06-22       Impact factor: 15.419

6.  Stereospecific Asymmetric Synthesis of Tertiary Allylic Alcohol Derivatives by Catalytic [2,3]-Meisenheimer Rearrangements.

Authors:  Xin Yu; Nick Wannenmacher; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-30       Impact factor: 15.336

  6 in total

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