Literature DB >> 17910469

Synthesis of tertiary alpha-hydroxy acids by silylene transfer to alpha-keto esters.

Brett E Howard1, K A Woerpel.   

Abstract

Alpha-keto esters can be converted into alpha-hydroxy acids in a single flask involving metal-catalyzed silylene transfer, 6pi-electrocyclization, Ireland-Claisen rearrangement, and hydrolysis. This reaction sequence is stereoselective and tolerates alkyl- and aryl-substituted alpha-keto ester substrates as well as an alpha-imino ester.

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Year:  2007        PMID： 17910469     DOI： 10.1021/ol702148x

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


  4 in total

1.  Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes.

Authors:  Paul Spaltenstein; Elizabeth J Cummins; Kelly-Marie Yokuda; Tim Kowalczyk; Timothy B Clark; Gregory W O'Neil
Journal:  J Org Chem       Date:  2019-03-13       Impact factor: 4.354

2.  Silylene transfer to alpha-keto esters and application to the synthesis of gamma-lactones.

Authors:  Brett E Howard; K A Woerpel
Journal:  Tetrahedron       Date:  2009-09-01       Impact factor: 2.457

3.  Synthesis of gamma,delta-unsaturated glycolic acids via sequenced brook and Ireland--claisen rearrangements.

Authors:  Daniel C Schmitt; Jeffrey S Johnson
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

4.  Continuous flow based catch and release protocol for the synthesis of alpha-ketoesters.

Authors:  Alessandro Palmieri; Steven V Ley; Anastasios Polyzos; Mark Ladlow; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2009-05-20       Impact factor: 2.883
  4 in total

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