Literature DB >> 16048342

Cationic rhodium(I)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to alpha,beta-enones.

Ken Tanaka1, Takeaki Shoji.   

Abstract

We have developed a cationic rhodium(I)/BINAP complex-catalyzed isomerization of secondary propargylic alcohols to alpha,beta-enones. The asymmetric variant of this reaction, a kinetic resolution of secondary propargylic alcohols, was also developed with good selectivity. The mechanistic study revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. [reaction: see text]

Entities:  

Year:  2005        PMID： 16048342     DOI： 10.1021/ol051335u

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


  4 in total

1.  An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.

Authors:  Barry M Trost; Robert C Livingston
Journal:  J Am Chem Soc       Date:  2008-08-15       Impact factor: 15.419

2.  Divergent Mechanisms of the Banert Cascade with Propargyl Azides.

Authors:  Juliana R Alexander; Mary H Packard; Alanna M Hildebrandt; Amy A Ott; Joseph J Topczewski
Journal:  J Org Chem       Date:  2020-01-24       Impact factor: 4.354

3.  Stereocontrol in Palladium-Catalyzed Propargylic Substitutions: Kinetic Resolution to give Enantioenriched 1,5-Enynes and Propargyl Acetates.

Authors:  Michael J Ardolino; Meredith S Eno; James P Morken
Journal:  Adv Synth Catal       Date:  2013-11-25       Impact factor: 5.837

Review 4.  Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones.

Authors:  Pakorn Bovonsombat; Punyanuch Sophanpanichkul; Satreerat Losuwanakul
Journal:  RSC Adv       Date:  2022-08-12       Impact factor: 4.036
  4 in total

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