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Synthesis 2013; 45(10): 1406-1413
DOI: 10.1055/s-0032-1316917
DOI: 10.1055/s-0032-1316917
paper
(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins
Authors
Weitere Informationen
Publikationsverlauf
Received: 04. Januar 2013
Accepted after revision: 19. März 2013
Publikationsdatum:
12. April 2013 (online)
Abstract
(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from l-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to β-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various γ-nitro carbonyl compounds in high yield (up to 97%) with excellent stereoselectivity (up to >99:1 dr and >99% ee) without the use of any additive.
Supporting Information
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Wet toluene was obtained by shaking toluene (100 mL) with H2O (10 mL). The separated toluene layer was used as such in the reactions. Water is known to play a significant role in the enamine catalytic cycle, including in the regeneration of catalyst; see ref. 4e and:
We are grateful to the reviewers for pointing out our oversight in not elaborating on the chirality aspect of the sulfur atom in compounds 6 and 1. The proposed transition states have also been modified as per their suggestions. For Seebach’s model, see: