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C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones.
Org Biomol Chem. 2012 May 14; 10(18):3721-9.OB

Abstract

A C(2)-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of diastereo- and enantioselectivities (up to >99 : 1 dr and 93% ee) under mild conditions. By studying the ESI-MS of the intermediates, a proposed mechanism was disclosed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ma S
Department of Chemistry, The Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China.
Wu L
No affiliation info available
Liu M
No affiliation info available
Wang Y
No affiliation info available

MeSH

AminesCatalysisChalconesKetonesMolecular StructureProlineStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

22447107

Citation

Ma, Shijun, et al. "C2-symmetric Proline-derived Tetraamine as Highly Effective Catalyst for Direct Asymmetric Michael Addition of Ketones to Chalcones." Organic & Biomolecular Chemistry, vol. 10, no. 18, 2012, pp. 3721-9.
Ma S, Wu L, Liu M, et al. C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones. Org Biomol Chem. 2012;10(18):3721-9.
Ma, S., Wu, L., Liu, M., & Wang, Y. (2012). C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones. Organic & Biomolecular Chemistry, 10(18), 3721-9. https://doi.org/10.1039/c2ob06897d
Ma S, et al. C2-symmetric Proline-derived Tetraamine as Highly Effective Catalyst for Direct Asymmetric Michael Addition of Ketones to Chalcones. Org Biomol Chem. 2012 May 14;10(18):3721-9. PubMed PMID: 22447107.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - C2-symmetric proline-derived tetraamine as highly effective catalyst for direct asymmetric Michael addition of ketones to chalcones. AU - Ma,Shijun, AU - Wu,Lulu, AU - Liu,Ming, AU - Wang,Yongmei, Y1 - 2012/03/26/ PY - 2012/3/27/entrez PY - 2012/3/27/pubmed PY - 2012/10/10/medline SP - 3721 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 18 N2 - A C(2)-symmetric tetraamine catalyst was developed for the asymmetric Michael addition of ketones to chalcones. The corresponding adducts 1,5-dicarbonyl compounds were obtained in good chemical yields with high levels of diastereo- and enantioselectivities (up to >99 : 1 dr and 93% ee) under mild conditions. By studying the ESI-MS of the intermediates, a proposed mechanism was disclosed. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22447107/C2_symmetric_proline_derived_tetraamine_as_highly_effective_catalyst_for_direct_asymmetric_Michael_addition_of_ketones_to_chalcones_ L2 - https://doi.org/10.1039/c2ob06897d DB - PRIME DP - Unbound Medicine ER -