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Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.
J Org Chem. 2007 Jul 06; 72(14):5457-60.JO

Abstract

The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1'-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the presence of Et2Zn in good yields and excellent enantioselectivities of up to 94% ee at room temperature. The mild reaction conditions make it possible to use functional alkynes in this asymmetric addition.

Authors+Show Affiliations

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

17555361

Citation

Yang, Fei, et al. "Facile, Mild, and Highly Enantioselective Alkynylzinc Addition to Aromatic Aldehydes By BINOL/N-methylimidazole Dual Catalysis." The Journal of Organic Chemistry, vol. 72, no. 14, 2007, pp. 5457-60.
Yang F, Xi P, Yang L, et al. Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis. J Org Chem. 2007;72(14):5457-60.
Yang, F., Xi, P., Yang, L., Lan, J., Xie, R., & You, J. (2007). Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis. The Journal of Organic Chemistry, 72(14), 5457-60.
Yang F, et al. Facile, Mild, and Highly Enantioselective Alkynylzinc Addition to Aromatic Aldehydes By BINOL/N-methylimidazole Dual Catalysis. J Org Chem. 2007 Jul 6;72(14):5457-60. PubMed PMID: 17555361.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis. AU - Yang,Fei, AU - Xi,Peihua, AU - Yang,Li, AU - Lan,Jingbo, AU - Xie,Rugang, AU - You,Jingsong, Y1 - 2007/06/08/ PY - 2007/6/9/pubmed PY - 2007/8/19/medline PY - 2007/6/9/entrez SP - 5457 EP - 60 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 14 N2 - The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1'-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the presence of Et2Zn in good yields and excellent enantioselectivities of up to 94% ee at room temperature. The mild reaction conditions make it possible to use functional alkynes in this asymmetric addition. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17555361/Facile_mild_and_highly_enantioselective_alkynylzinc_addition_to_aromatic_aldehydes_by_BINOL/N_methylimidazole_dual_catalysis_ L2 - https://doi.org/10.1021/jo0707535 DB - PRIME DP - Unbound Medicine ER -