Tags

Type your tag names separated by a space and hit enter

A new class of urea-substituted cinchona alkaloids promote highly enantioselective nitroaldol reactions of trifluoromethylketones.
Org Lett. 2011 Mar 18; 13(6):1298-301.OL

Abstract

The first class of bifunctional cinchona-alkaloid catalysts incorporating a urea moiety at C-5' has been developed. These materials catalyze the efficient and highly enantioselective 1,2-addition of nitromethane to trifluoromethylketones to form synthetically pliable products incorporating a quaternary stereocenter. Excellent product yields and levels of enantiomeric excess are possible, and the optimum catalyst structure is capable of promoting the Henry reaction involving alkyl trifluoromethylketones with unprecedented enantioselectivity.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Palacio C
Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
Connon SJ
No affiliation info available

MeSH

AldehydesCinchona AlkaloidsCombinatorial Chemistry TechniquesHydrocarbons, FluorinatedKetonesNitro CompoundsStereoisomerismUrea

Pub Type(s)

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

Language

eng

PubMed ID

21338077

Citation

Palacio, Carole, and Stephen J. Connon. "A New Class of Urea-substituted Cinchona Alkaloids Promote Highly Enantioselective Nitroaldol Reactions of Trifluoromethylketones." Organic Letters, vol. 13, no. 6, 2011, pp. 1298-301.
Palacio C, Connon SJ. A new class of urea-substituted cinchona alkaloids promote highly enantioselective nitroaldol reactions of trifluoromethylketones. Org Lett. 2011;13(6):1298-301.
Palacio, C., & Connon, S. J. (2011). A new class of urea-substituted cinchona alkaloids promote highly enantioselective nitroaldol reactions of trifluoromethylketones. Organic Letters, 13(6), 1298-301. https://doi.org/10.1021/ol103089j
Palacio C, Connon SJ. A New Class of Urea-substituted Cinchona Alkaloids Promote Highly Enantioselective Nitroaldol Reactions of Trifluoromethylketones. Org Lett. 2011 Mar 18;13(6):1298-301. PubMed PMID: 21338077.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A new class of urea-substituted cinchona alkaloids promote highly enantioselective nitroaldol reactions of trifluoromethylketones. AU - Palacio,Carole, AU - Connon,Stephen J, Y1 - 2011/02/21/ PY - 2011/2/23/entrez PY - 2011/2/23/pubmed PY - 2011/6/15/medline SP - 1298 EP - 301 JF - Organic letters JO - Org Lett VL - 13 IS - 6 N2 - The first class of bifunctional cinchona-alkaloid catalysts incorporating a urea moiety at C-5' has been developed. These materials catalyze the efficient and highly enantioselective 1,2-addition of nitromethane to trifluoromethylketones to form synthetically pliable products incorporating a quaternary stereocenter. Excellent product yields and levels of enantiomeric excess are possible, and the optimum catalyst structure is capable of promoting the Henry reaction involving alkyl trifluoromethylketones with unprecedented enantioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21338077/A_new_class_of_urea_substituted_cinchona_alkaloids_promote_highly_enantioselective_nitroaldol_reactions_of_trifluoromethylketones_ L2 - https://doi.org/10.1021/ol103089j DB - PRIME DP - Unbound Medicine ER -