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Synfacts 2009(8): 0910-0910
DOI: 10.1055/s-0029-1217592
DOI: 10.1055/s-0029-1217592
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Mannich Reaction of Sulfonylacetates
C. Cassani, L. Bernardi*, F. Fini, A. Ricci*
University of Bologna, Italy
Further Information
Publication History
Publication Date:
23 July 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200908/lookinside/thumbnails/10.1055-s-0029-1217592-1.jpg)
Significance
Ricci, Bernardi and co-workers report a phase-transfer-catalyzed enantioselective Mannich addition of arylsulfonylacetates to highly reactive N-carbamoyl imines generated in situ from α-amidosulfones. Reductive removal of the sulfonyl group of the Mannich adducts yields the corresponding N-Boc- or N-Cbz-protected β³-amino-esters whereas a Julia-type olefination gives access to aza-Morita-Baylis-Hillman-type products. This transformation was carried out with different linear, α- or β-branched, and aromatic α-amido-sulfones in moderate to good yields with high enantioselectivities.