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Diarylprolinol Silyl Ether Salts as New, Efficient, Water-Soluble, and Recyclable Organocatalysts for the Asymmetric Michael Addition on Water

Zilong Zheng, Benjamin L. Perkins and Bukuo Ni*

*Department of Chemistry, Texas A&M University-Commerce, Commerce, Texas 75429-3011, Email: bukuo_nitamu-commerce.edu

Z. Zheng, B. L. Perksin, B. Ni, J. Am. Chem. Soc., 2010, 132, 50-51.

DOI: 10.1021/ja9093583 (free Supporting Information)


Abstract

A simple, practical, and environmentally benign asymmetric Michael addition of aldehydes to nitroolefins on water provided Michael adducts in excellent diastereo- and enantioselectivities in the presence of a water-soluble organocatalyst. The catalyst can be recycled for more than six times without a significant loss of activity and stereochemical control.

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A Novel Recyclable Organocatalytic System for the Highly Asymmetric Michael Addition of Aldehydes to Nitroolefins in Water

D. Sarkar, R. Bhattarai, A. D. Headley, B. Ni, Synthesis, 2011, 1993-1997.


Key Words

Nitro Compounds, Organocatalysis, Green Chemistry


ID: J48-Y2010-0080