Literature DB >> 11798313

P(RNCH(2)CH(2))(3)N-catalyzed 1,2-addition reactions of activated allylic synthons.

Philip B Kisanga1, John G Verkade.   

Abstract

Activated allylic compounds of the type RCH:CHCH(2)Z (Z = CN, CO(2)Me) react efficiently with aromatic aldehydes in the presence of 20-40 mol % of P(R'NCH(2)CH(2))(3)N at -94 to -63 degrees C. Both R = H and R = Me lead exclusively to alpha-addition products. When R = H and Z = CN, an allylic transposition occurs to afford a Baylis-Hillman product as the only product.

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Year:  2002        PMID: 11798313     DOI: 10.1021/jo0106492

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


  2 in total

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Authors:  Scott E Denmark; Tyler W Wilson
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-20       Impact factor: 15.336

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Authors:  Jeremy Kister; Daniel H Ess; William R Roush
Journal:  Org Lett       Date:  2013-10-18       Impact factor: 6.005

  2 in total

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