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A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water.
Org Lett. 2006 Jul 06; 8(14):3077-9.OL

Abstract

[reaction: see text] A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity.

Authors+Show Affiliations

Zu L
Department of Chemistry, University of New Mexico, Albuquerque, 87131-0001, USA.
Wang J
No affiliation info available
Li H
No affiliation info available
Wang W
No affiliation info available

MeSH

AldehydesAlkenesCombinatorial Chemistry TechniquesHydrocarbons, FluorinatedKetonesNitro CompoundsPyrrolidinesStereoisomerismSulfonamidesWater

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16805556

Citation

Zu, Liansuo, et al. "A Recyclable Fluorous (S)-pyrrolidine Sulfonamide Promoted Direct, Highly Enantioselective Michael Addition of Ketones and Aldehydes to Nitroolefins in Water." Organic Letters, vol. 8, no. 14, 2006, pp. 3077-9.
Zu L, Wang J, Li H, et al. A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. Org Lett. 2006;8(14):3077-9.
Zu, L., Wang, J., Li, H., & Wang, W. (2006). A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. Organic Letters, 8(14), 3077-9.
Zu L, et al. A Recyclable Fluorous (S)-pyrrolidine Sulfonamide Promoted Direct, Highly Enantioselective Michael Addition of Ketones and Aldehydes to Nitroolefins in Water. Org Lett. 2006 Jul 6;8(14):3077-9. PubMed PMID: 16805556.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. AU - Zu,Liansuo, AU - Wang,Jian, AU - Li,Hao, AU - Wang,Wei, PY - 2006/6/30/pubmed PY - 2007/4/27/medline PY - 2006/6/30/entrez SP - 3077 EP - 9 JF - Organic letters JO - Org Lett VL - 8 IS - 14 N2 - [reaction: see text] A recycle and reusable fluorous (S)-pyrrolidine sulfonamide organocatalyst has been developed for promoting highly enantio- and diastereoselective Michael addition reactions of ketones and aldehydes with nitroolefins in water. The organocatalyst is conveniently recovered from the reaction mixtures by fluorous solid-phase extraction and can be subsequently reused (up to six cycles) without a significant loss of catalytic activity and stereoselectivity. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16805556/A_recyclable_fluorous__S__pyrrolidine_sulfonamide_promoted_direct_highly_enantioselective_Michael_addition_of_ketones_and_aldehydes_to_nitroolefins_in_water_ L2 - https://doi.org/10.1021/ol061053+ DB - PRIME DP - Unbound Medicine ER -