Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media

Subrata K Ghosh; Kritanjali Dhungana; Allan D Headley; Bukuo Ni

doi:10.1039/c2ob26248g

Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media

Org Biomol Chem. 2012 Oct 3;10(41):8322-5. doi: 10.1039/c2ob26248g.

Authors

Subrata K Ghosh¹, Kritanjali Dhungana, Allan D Headley, Bukuo Ni

Affiliation

¹ Department of Chemistry, Texas A&M University-Commerce, 75429-3011, USA.

PMID: 22976596
DOI: 10.1039/c2ob26248g

Abstract

A new type of pyrrolidine-based organocatalyst, which was developed earlier in our lab, has been found to be very effective for the Michael addition reaction in aqueous solvents involving a wide range of α,β-unsaturated aldehydes and malonate derivatives. For the reactions studied, good to excellent yields (73%-96%) and high to excellent enantioselectivities (up to 97%) were obtained using this catalyst. In addition, the catalyst could be recycled up to four times with gradual reductions in yields and enantioselectivity observed after the second cycle.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Aldehydes / chemistry*
Catalysis
Malonates / chemistry*
Molecular Structure
Pyrrolidines / chemistry
Stereoisomerism
Water / chemistry*

Substances

Aldehydes
Malonates
Pyrrolidines
Water
malonic acid
pyrrolidine