(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins

Kamal Nain Singh; Paramjit Singh; Amarjit Kaur; Pushpinder Singh; Sandeep Kumar Sharma; Sadhika Khullar; Sanjay K. Mandal

doi:10.1055/s-0032-1316917

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1406-1413
DOI: 10.1055/s-0032-1316917

paper

(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins

Kamal Nain Singh*

^aDepartment of Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 Email: kns@pu.ac.in

,

Paramjit Singh

^aDepartment of Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 Email: kns@pu.ac.in

,

Amarjit Kaur

^aDepartment of Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 Email: kns@pu.ac.in

,

Pushpinder Singh

^aDepartment of Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 Email: kns@pu.ac.in

,

Sandeep Kumar Sharma

^aDepartment of Chemistry, Panjab University, Chandigarh 160014, India Fax: +91(172)2545074 Email: kns@pu.ac.in

,

Sadhika Khullar

^bDepartment of Chemical Sciences, Indian Institute of Science Education and Research, Mohali, Sector 81, Manauli PO, S.A.S. Nagar, Mohali (Punjab) 140306, India

,

Sanjay K. Mandal

^bDepartment of Chemical Sciences, Indian Institute of Science Education and Research, Mohali, Sector 81, Manauli PO, S.A.S. Nagar, Mohali (Punjab) 140306, India

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Abstract

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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.

Key words

Michael addition reaction - organocatalyst - amino sulfoxide - nitroolefins - ketones

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References

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Supplementary Material

Supporting Information