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Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes.
J Org Chem. 2005 Feb 04; 70(3):1084-6.JO

Abstract

The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols.

Authors+Show Affiliations

Liu L
Department of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, Gansu 730000, China.
Wang R
No affiliation info available
Kang YF
No affiliation info available
Chen C
No affiliation info available
Xu ZQ
No affiliation info available
Zhou YF
No affiliation info available
Ni M
No affiliation info available
Cai HQ
No affiliation info available
Gong MZ
No affiliation info available

MeSH

AcetyleneAluminumCatalysisCinchona AlkaloidsHydrocarbons, AromaticKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15675878

Citation

Liu, Lei, et al. "Highly Enantioselective Phenylacetylene Addition to Aromatic Ketones Catalyzed By Cinchona Alkaloid-aluminum Complexes." The Journal of Organic Chemistry, vol. 70, no. 3, 2005, pp. 1084-6.
Liu L, Wang R, Kang YF, et al. Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes. J Org Chem. 2005;70(3):1084-6.
Liu, L., Wang, R., Kang, Y. F., Chen, C., Xu, Z. Q., Zhou, Y. F., Ni, M., Cai, H. Q., & Gong, M. Z. (2005). Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes. The Journal of Organic Chemistry, 70(3), 1084-6.
Liu L, et al. Highly Enantioselective Phenylacetylene Addition to Aromatic Ketones Catalyzed By Cinchona Alkaloid-aluminum Complexes. J Org Chem. 2005 Feb 4;70(3):1084-6. PubMed PMID: 15675878.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly enantioselective phenylacetylene addition to aromatic ketones catalyzed by cinchona alkaloid-aluminum complexes. AU - Liu,Lei, AU - Wang,Rui, AU - Kang,Yong-Feng, AU - Chen,Chao, AU - Xu,Zhao-Qing, AU - Zhou,Yi-Feng, AU - Ni,Ming, AU - Cai,Hua-Qing, AU - Gong,Mao-Zhen, PY - 2005/1/29/pubmed PY - 2005/6/1/medline PY - 2005/1/29/entrez SP - 1084 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 3 N2 - The catalytic asymmetric addition of phenylacetylene to aromatic ketones is reported. The catalyst, generated from commercially available Cinchona alkaloids and industrially available triethylaluminum, gives the expected tertiary alcohols with good enantiomeric excess (70-89%) and yields (60-83%). No previous case has been reported successfully using triethylaluminum as a Lewis acid in the asymmetric alkynylation of carbonylic derivatives, and thus we provide a new method to obtain optically active tertiary propargyl alcohols. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15675878/Highly_enantioselective_phenylacetylene_addition_to_aromatic_ketones_catalyzed_by_cinchona_alkaloid_aluminum_complexes_ DB - PRIME DP - Unbound Medicine ER -