Literature DB >> 11667544

Diastereoselective Rh-Mediated Construction of 2,3,5-Trisubstituted Tetrahydrofurans.

Douglass F. Taber1, Ying Song.   

Abstract

Dirhodium(II) carboxylate catalyzed cyclization of a series of gamma-alkoxy-alpha-diazo esters 1 has been shown to proceed with substantial diastereoselectivity, producing the 2,3,5-trisubstituted tetrahydrofurans 2 and 3. The diastereoselectivity of the cyclization improved as the electron-withdrawing ability of the substituent R increased. A mechanistic hypothesis is presented.

Entities:  

Year:  1996        PMID： 11667544     DOI： 10.1021/jo960758u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors:  John P Wolfe; Michael B Hay
Journal:  Tetrahedron       Date:  2007-01-08       Impact factor: 2.457

Review 2.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

3.  Rh-catalyzed intermolecular reactions of cyclic α-diazocarbonyl compounds with selectivity over tertiary C-H bond migration.

Authors:  Andrew DeAngelis; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2012-06-19       Impact factor: 15.419

Review 4.  The synthesis of functionalized bridged polycycles via C-H bond insertion.

Authors:  Jiun-Le Shih; Po-An Chen; Jeremy A May
Journal:  Beilstein J Org Chem       Date:  2016-05-17       Impact factor: 2.883
  4 in total

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