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Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine.
Org Lett. 2014 Sep 05; 16(17):4626-9.OL

Abstract

The first effective example of asymmetric conjugate addition-protonation reactions of thiols to α-substituted vinyl ketones by chiral primary amine catalysis is reported. A simple chiral primary-tertiary diamine catalyst derived from l-phenylalanine was found to promote the sulfa-Michael addition-protonation reactions with good to excellent enantioselectivity.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fu N
Beijing National Laboratory for Molecule Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences , Beijing, 100190, P.R. China.
Zhang L
No affiliation info available
Luo S
No affiliation info available
Cheng JP
No affiliation info available

MeSH

AminesCatalysisDiaminesKetonesMolecular StructurePhenylalanineStereoisomerismSulfhydryl CompoundsVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

25144533

Citation

Fu, Niankai, et al. "Asymmetric sulfa-Michael Addition to Α-substituted Vinyl Ketones Catalyzed By Chiral Primary Amine." Organic Letters, vol. 16, no. 17, 2014, pp. 4626-9.
Fu N, Zhang L, Luo S, et al. Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine. Org Lett. 2014;16(17):4626-9.
Fu, N., Zhang, L., Luo, S., & Cheng, J. P. (2014). Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine. Organic Letters, 16(17), 4626-9. https://doi.org/10.1021/ol5022178
Fu N, et al. Asymmetric sulfa-Michael Addition to Α-substituted Vinyl Ketones Catalyzed By Chiral Primary Amine. Org Lett. 2014 Sep 5;16(17):4626-9. PubMed PMID: 25144533.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric sulfa-Michael addition to α-substituted vinyl ketones catalyzed by chiral primary amine. AU - Fu,Niankai, AU - Zhang,Long, AU - Luo,Sanzhong, AU - Cheng,Jin-Pei, Y1 - 2014/08/21/ PY - 2014/8/22/entrez PY - 2014/8/22/pubmed PY - 2015/6/6/medline SP - 4626 EP - 9 JF - Organic letters JO - Org Lett VL - 16 IS - 17 N2 - The first effective example of asymmetric conjugate addition-protonation reactions of thiols to α-substituted vinyl ketones by chiral primary amine catalysis is reported. A simple chiral primary-tertiary diamine catalyst derived from l-phenylalanine was found to promote the sulfa-Michael addition-protonation reactions with good to excellent enantioselectivity. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25144533/Asymmetric_sulfa_Michael_addition_to_α_substituted_vinyl_ketones_catalyzed_by_chiral_primary_amine_ DB - PRIME DP - Unbound Medicine ER -