Tags

Type your tag names separated by a space and hit enter

L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins.
Bioorg Med Chem Lett. 2009 Jul 15; 19(14):3915-8.BM

Abstract

Though many chiral amines such as l-proline and its derivatives have proven to be versatile catalysts in many reactions, L-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first L-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13->99:1) and enantioselectivities (82-96%).

Links

Publisher Full Text

Authors+Show Affiliations

Chua PJ
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, Singapore.
Tan B
No affiliation info available
Zeng X
No affiliation info available
Zhong G
No affiliation info available

MeSH

AlkenesBenzoic AcidCatalysisCyclohexanonesPyrrolidinesStereoisomerismTemperature

Pub Type(s)

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

Language

eng

PubMed ID

19359171

Citation

Chua, Pei Juan, et al. "L-prolinol as a Highly Enantioselective Catalyst for Michael Addition of Cyclohexanone to Nitroolefins." Bioorganic & Medicinal Chemistry Letters, vol. 19, no. 14, 2009, pp. 3915-8.
Chua PJ, Tan B, Zeng X, et al. L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins. Bioorg Med Chem Lett. 2009;19(14):3915-8.
Chua, P. J., Tan, B., Zeng, X., & Zhong, G. (2009). L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins. Bioorganic & Medicinal Chemistry Letters, 19(14), 3915-8. https://doi.org/10.1016/j.bmcl.2009.03.076
Chua PJ, et al. L-prolinol as a Highly Enantioselective Catalyst for Michael Addition of Cyclohexanone to Nitroolefins. Bioorg Med Chem Lett. 2009 Jul 15;19(14):3915-8. PubMed PMID: 19359171.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins. AU - Chua,Pei Juan, AU - Tan,Bin, AU - Zeng,Xiaofei, AU - Zhong,Guofu, Y1 - 2009/03/25/ PY - 2009/02/01/received PY - 2009/03/19/revised PY - 2009/03/20/accepted PY - 2009/4/11/entrez PY - 2009/4/11/pubmed PY - 2009/10/29/medline SP - 3915 EP - 8 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 19 IS - 14 N2 - Though many chiral amines such as l-proline and its derivatives have proven to be versatile catalysts in many reactions, L-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first L-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13->99:1) and enantioselectivities (82-96%). SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/19359171/L_prolinol_as_a_highly_enantioselective_catalyst_for_Michael_addition_of_cyclohexanone_to_nitroolefins_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(09)00391-6 DB - PRIME DP - Unbound Medicine ER -