P(RNCH2CH2)3N: Efficient 1,4-Addition Catalysts
- 30 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (11), 3555-3560
- https://doi.org/10.1021/jo010228k
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.Keywords
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