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Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media.
Org Biomol Chem. 2012 Oct 03; 10(41):8322-5.OB

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ghosh SK
Department of Chemistry, Texas A&M University-Commerce, 75429-3011, USA.
Dhungana K
No affiliation info available
Headley AD
No affiliation info available
Ni B
No affiliation info available

MeSH

AldehydesCatalysisMalonatesMolecular StructurePyrrolidinesStereoisomerismWater

Pub Type(s)

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

Language

eng

PubMed ID

22976596

Citation

Ghosh, Subrata K., et al. "Highly Enantioselective and Recyclable Organocatalytic Michael Addition of Malonates to Α,β-unsaturated Aldehydes in Aqueous Media." Organic & Biomolecular Chemistry, vol. 10, no. 41, 2012, pp. 8322-5.
Ghosh SK, Dhungana K, Headley AD, et al. Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media. Org Biomol Chem. 2012;10(41):8322-5.
Ghosh, S. K., Dhungana, K., Headley, A. D., & Ni, B. (2012). Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media. Organic & Biomolecular Chemistry, 10(41), 8322-5. https://doi.org/10.1039/c2ob26248g
Ghosh SK, et al. 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. PubMed PMID: 22976596.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective and recyclable organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in aqueous media. AU - Ghosh,Subrata K, AU - Dhungana,Kritanjali, AU - Headley,Allan D, AU - Ni,Bukuo, PY - 2012/9/15/entrez PY - 2012/9/15/pubmed PY - 2013/2/22/medline SP - 8322 EP - 5 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 41 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22976596/Highly_enantioselective_and_recyclable_organocatalytic_Michael_addition_of_malonates_to_αβ_unsaturated_aldehydes_in_aqueous_media_ L2 - https://doi.org/10.1039/c2ob26248g DB - PRIME DP - Unbound Medicine ER -