Literature DB >> 11678708

Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions.

J Hassfeld1, M Christmann, M Kalesse.   

Abstract

[reaction: see text]. The use of the Z-configured vinylogous silyl ketene acetals in Mukaiyama aldol reactions is described. Isopropyl alcohol as scavanger and the use of tris(pentafluorophenyl)borane as the Lewis acid are required for obtaining the gamma-alkylated syn-product selectively. In cases of alpha-chiral aldehydes, Felkin-Anh selectivity was observed.

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Year:  2001        PMID： 11678708     DOI： 10.1021/ol016677o

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


  3 in total

1.  Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion.

Authors:  Jie Wu; Yu Chen; James S Panek
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

2.  Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.

Authors:  Wildeliz Torres; Raúl R Rodríguez; José A Prieto
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

3.  Stereoselective synthesis of highly functionalized alpha-diazo-beta-ketoalkanoates via catalytic one-pot Mukaiyama-Aldol reactions.

Authors:  Lei Zhou; Michael P Doyle
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005
  3 in total

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