Ferrocene Analogues of Hydrogen-Bond-Donor Catalysts: An Investigative Study on Asymmetric Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes

Kadiyala Srinivasa Rao; Rajiv Trivedi; M. Lakshmi Kantam

doi:10.1055/s-0034-1379491

Synlett, Table of Contents

Synlett 2015; 26(02): 221-227
DOI: 10.1055/s-0034-1379491

letter

Ferrocene Analogues of Hydrogen-Bond-Donor Catalysts: An Investigative Study on Asymmetric Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes

Kadiyala Srinivasa Rao

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, Telangana 500007, India Email: trivedi@iict.res.in Email: rtrajiv401@gmail.com Fax: +91(40)27191667 Fax: +91(40)27160921

,

Rajiv Trivedi*

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, Telangana 500007, India Email: trivedi@iict.res.in Email: rtrajiv401@gmail.com Fax: +91(40)27191667 Fax: +91(40)27160921

,

M. Lakshmi Kantam

Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad, Telangana 500007, India Email: trivedi@iict.res.in Email: rtrajiv401@gmail.com Fax: +91(40)27191667 Fax: +91(40)27160921

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Abstract

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Abstract

This report describes the synthesis of eight ferrocene derivatives of squaramide- or thiourea- based bifunctional catalysts containing cinchona alkaloid moieties. A stepwise sequential route was used to assemble the various components of these ferrocene derivatives. The resulting bifunctional catalysts were used successfully in asymmetric Michael additions of 1,3-dicarbonyl compounds to β-nitrostyrenes. The corresponding products were obtained in high yields and in good to excellent enantioselectivities and diastereoselectivities under mild conditions by using 1 mol% of the catalyst.

Key words

Michael additions - asymmetric catalysis - ferrocenes - alkaloids - nitro compounds - dicarbonyl compounds

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References

References and Notes

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Supplementary Material

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