Asymmetric Tandem ConjugateAddition-Allylation of Chiral (p-Tolylsulfinyl)pyrrolylCinnamoyl Amide
- 8 July 2003
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2003 (10) , 1511-1516
- https://doi.org/10.1055/s-2003-40510
Abstract
The alkylation by allyl halides of the intermediate enolate, prepared in situ by conjugate addition of di-p-tolylcuprate to chiral (p-tolylsulfinyl)pyrrolyl cinnamoyl amide, gave the (2R,3R)-adducts as the major products with 81% to 94% de’s. Methanolysis of the products afforded the corresponding methyl esters, together with efficient recovery of the chiral sulfinyl auxiliary without loss of optical purity.Keywords
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