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Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones.
Org Lett. 2007 Feb 01; 9(3):413-5.OL

Abstract

[reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee).

Authors+Show Affiliations

Xie JW
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, China.
Yue L
No affiliation info available
Chen W
No affiliation info available
Du W
No affiliation info available
Zhu J
No affiliation info available
Deng JG
No affiliation info available
Chen YC
No affiliation info available

MeSH

AldehydesAminesAnticoagulantsCatalysisCyclizationKetonesModels, ChemicalModels, MolecularQuinineSolventsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17249775

Citation

Xie, Jian-Wu, et al. "Highly Enantioselective Michael Addition of Cyclic 1,3-dicarbonyl Compounds to Alpha,beta-unsaturated Ketones." Organic Letters, vol. 9, no. 3, 2007, pp. 413-5.
Xie JW, Yue L, Chen W, et al. Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones. Org Lett. 2007;9(3):413-5.
Xie, J. W., Yue, L., Chen, W., Du, W., Zhu, J., Deng, J. G., & Chen, Y. C. (2007). Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones. Organic Letters, 9(3), 413-5.
Xie JW, et al. Highly Enantioselective Michael Addition of Cyclic 1,3-dicarbonyl Compounds to Alpha,beta-unsaturated Ketones. Org Lett. 2007 Feb 1;9(3):413-5. PubMed PMID: 17249775.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective michael addition of cyclic 1,3-dicarbonyl compounds to alpha,beta-unsaturated ketones. AU - Xie,Jian-Wu, AU - Yue,Lei, AU - Chen,Wei, AU - Du,Wei, AU - Zhu,Jin, AU - Deng,Jin-Gen, AU - Chen,Ying-Chun, PY - 2007/1/26/pubmed PY - 2007/4/10/medline PY - 2007/1/26/entrez SP - 413 EP - 5 JF - Organic letters JO - Org Lett VL - 9 IS - 3 N2 - [reaction: see text] The highly enantioselective Michael addition of 1,3-cyclic dicarbonyl compounds to alpha,beta-unsaturated ketones was reported to be catalyzed by an organic primary amine derived from quinine. A chiral anticoagulant drug, (S)-warfarin, was directly prepared in 96% ee, and other related important adducts were also obtained in excellent enantioselectivity (89-99% ee). SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17249775/Highly_enantioselective_michael_addition_of_cyclic_13_dicarbonyl_compounds_to_alphabeta_unsaturated_ketones_ L2 - https://doi.org/10.1021/ol062718a DB - PRIME DP - Unbound Medicine ER -