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Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones.
J Org Chem. 2012 Apr 20; 77(8):4136-42.JO

Abstract

A simple chiral diamine catalyst (1a) was successfully applied in the asymmetric Michael reaction between cyclic dimedone and α,β-unsaturated ketones. Both acyclic enones with aryl or alkyl β-substituents and cyclic enones were tolerated well in the reaction. The desired adducts were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee). The additives were found to increase the reactivity dramatically. The biologically active 2,4-disubstituted polyhydroquinoline scaffold was conveniently prepared through an ammoniation from the generated 3,4-dihydropyran product.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu Y
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Liu X
No affiliation info available
Wang M
No affiliation info available
He P
No affiliation info available
Lin L
No affiliation info available
Feng X
No affiliation info available

MeSH

CatalysisDiaminesKetonesMolecular StructurePyransStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22432769

Citation

Liu, Yangbin, et al. "Enantioselective Synthesis of 3,4-dihydropyran Derivatives Via Organocatalytic Michael Reaction of Α,β-unsaturated Enones." The Journal of Organic Chemistry, vol. 77, no. 8, 2012, pp. 4136-42.
Liu Y, Liu X, Wang M, et al. Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones. J Org Chem. 2012;77(8):4136-42.
Liu, Y., Liu, X., Wang, M., He, P., Lin, L., & Feng, X. (2012). Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones. The Journal of Organic Chemistry, 77(8), 4136-42. https://doi.org/10.1021/jo3001047
Liu Y, et al. Enantioselective Synthesis of 3,4-dihydropyran Derivatives Via Organocatalytic Michael Reaction of Α,β-unsaturated Enones. J Org Chem. 2012 Apr 20;77(8):4136-42. PubMed PMID: 22432769.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of 3,4-dihydropyran derivatives via organocatalytic Michael reaction of α,β-unsaturated enones. AU - Liu,Yangbin, AU - Liu,Xiaohua, AU - Wang,Min, AU - He,Peng, AU - Lin,Lili, AU - Feng,Xiaoming, Y1 - 2012/03/29/ PY - 2012/3/22/entrez PY - 2012/3/22/pubmed PY - 2012/8/2/medline SP - 4136 EP - 42 JF - The Journal of organic chemistry JO - J Org Chem VL - 77 IS - 8 N2 - A simple chiral diamine catalyst (1a) was successfully applied in the asymmetric Michael reaction between cyclic dimedone and α,β-unsaturated ketones. Both acyclic enones with aryl or alkyl β-substituents and cyclic enones were tolerated well in the reaction. The desired adducts were obtained in high yields (up to 98%) with excellent enantioselectivities (up to 97% ee). The additives were found to increase the reactivity dramatically. The biologically active 2,4-disubstituted polyhydroquinoline scaffold was conveniently prepared through an ammoniation from the generated 3,4-dihydropyran product. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/22432769/Enantioselective_synthesis_of_34_dihydropyran_derivatives_via_organocatalytic_Michael_reaction_of_αβ_unsaturated_enones_ L2 - https://doi.org/10.1021/jo3001047 DB - PRIME DP - Unbound Medicine ER -