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Highly enantioselective and regioselective substitution of Morita-Baylis-Hillman carbonates with nitroalkanes.
Org Lett. 2011 Nov 18; 13(22):6070-3.OL

Abstract

A highly enantioselective and regioselective substitution reaction of the Morita-Baylis-Hillman (MBH) carbonates with nitroalkanes catalyzed by a quinidine-derived tertiary amine-thiourea catalyst has been developed. The described method, which is different from most organocatalytic allylic substitutions of the MBH adducts to date, represents a novel approach to regioselectively functionalize the MBH adducts.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Chen GY
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.
Zhong F
No affiliation info available
Lu Y
No affiliation info available

MeSH

AlkanesCarbonatesCatalysisMolecular StructureNitro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22035214

Citation

Chen, Guo-Ying, et al. "Highly Enantioselective and Regioselective Substitution of Morita-Baylis-Hillman Carbonates With Nitroalkanes." Organic Letters, vol. 13, no. 22, 2011, pp. 6070-3.
Chen GY, Zhong F, Lu Y. Highly enantioselective and regioselective substitution of Morita-Baylis-Hillman carbonates with nitroalkanes. Org Lett. 2011;13(22):6070-3.
Chen, G. Y., Zhong, F., & Lu, Y. (2011). Highly enantioselective and regioselective substitution of Morita-Baylis-Hillman carbonates with nitroalkanes. Organic Letters, 13(22), 6070-3. https://doi.org/10.1021/ol202555v
Chen GY, Zhong F, Lu Y. Highly Enantioselective and Regioselective Substitution of Morita-Baylis-Hillman Carbonates With Nitroalkanes. Org Lett. 2011 Nov 18;13(22):6070-3. PubMed PMID: 22035214.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective and regioselective substitution of Morita-Baylis-Hillman carbonates with nitroalkanes. AU - Chen,Guo-Ying, AU - Zhong,Fangrui, AU - Lu,Yixin, Y1 - 2011/10/28/ PY - 2011/11/1/entrez PY - 2011/11/1/pubmed PY - 2012/2/22/medline SP - 6070 EP - 3 JF - Organic letters JO - Org Lett VL - 13 IS - 22 N2 - A highly enantioselective and regioselective substitution reaction of the Morita-Baylis-Hillman (MBH) carbonates with nitroalkanes catalyzed by a quinidine-derived tertiary amine-thiourea catalyst has been developed. The described method, which is different from most organocatalytic allylic substitutions of the MBH adducts to date, represents a novel approach to regioselectively functionalize the MBH adducts. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/22035214/Highly_enantioselective_and_regioselective_substitution_of_Morita_Baylis_Hillman_carbonates_with_nitroalkanes_ L2 - https://doi.org/10.1021/ol202555v DB - PRIME DP - Unbound Medicine ER -