Literature DB >> 12027665

P(RNCH(2)CH(2))(3)N: efficient 1,4-addition catalysts.

Philip B Kisanga1, Palanichamy Ilankumaran, Brandon M Fetterly, John G Verkade.   

Abstract

The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an alpha-amino ester to alpha,beta-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70 degrees C in the presence of catalytic amounts of the nonionic strong bases P(RNCH(2)CH(2))(3)N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.

Entities:  

Year:  2002        PMID: 12027665     DOI: 10.1021/jo010228k

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


  3 in total

1.  Bisphosphine-catalyzed mixed double-Michael reactions: asymmetric synthesis of oxazolidines, thiazolidines, and pyrrolidines.

Authors:  Vardhineedi Sriramurthy; Gregg A Barcan; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2007-10-09       Impact factor: 15.419

2.  N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Authors:  Eric M Phillips; Matthias Riedrich; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

3.  Chiral aminophosphines as catalysts for enantioselective double-Michael indoline syntheses.

Authors:  San N Khong; Ohyun Kwon
Journal:  Molecules       Date:  2012-05-11       Impact factor: 4.411

  3 in total

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