Literature DB >> 11895388

Mechanistic study of the Mitsunobu reaction.

Chuljin Ahn1, Reuben Correia, Philip DeShong.   

Abstract

The Mitsunobu reaction occurs typically with inversion of configuration in secondary alcohol derivatives. In this paper, a mechanistic explanation for lactonizations of hindered alcohols under Mitsunobu conditions with retention is proposed. This involves the intermediacy of an acyloxyphosphonium salt followed by acyl transfer to the alcohol.

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Year:  2002        PMID: 11895388     DOI: 10.1021/jo001590m

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


  5 in total

1.  Triphenylphosphine Dibromide: A Simple One-pot Esterification Reagent.

Authors:  Christophe Salomé; Harold Kohn
Journal:  Tetrahedron       Date:  2009-01-10       Impact factor: 2.457

2.  Synthesis of N,N-Diethylbenzamides via a Non-Classical Mitsunobu Reaction.

Authors:  J Mason Hoffman; Justin N Miller; Margaret E Gardner; Danielle R LePar; Rongson Pongdee
Journal:  Synth Commun       Date:  2014-01-01       Impact factor: 2.007

3.  Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2.

Authors:  George R Pettit; Peter D Quistorf; Jeremy A Fry; Delbert L Herald; Ernest Hamel; Jean-Charles Chapuis
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050

4.  Advances and mechanistic insight on the catalytic Mitsunobu reaction using recyclable azo reagents.

Authors:  Daisuke Hirose; Martin Gazvoda; Janez Košmrlj; Tsuyoshi Taniguchi
Journal:  Chem Sci       Date:  2016-04-13       Impact factor: 9.825

Review 5.  Anomeric modification of carbohydrates using the Mitsunobu reaction.

Authors:  Julia Hain; Patrick Rollin; Werner Klaffke; Thisbe K Lindhorst
Journal:  Beilstein J Org Chem       Date:  2018-06-29       Impact factor: 2.883

  5 in total

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