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Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins.
J Am Chem Soc. 2008 Oct 29; 130(43):14052-3.JA

Abstract

A highly efficient nickel-catalyzed asymmetric alkylative coupling of alkynes, aldehydes, and dimethylzinc has been realized by using bulky spirobiindane phosphoramidite ligands, affording allylic alcohols with a tetrasubstituted olefin functionality in high yields, high regioselectivities, and excellent enantioselectivities.

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Authors+Show Affiliations

Yang Y
State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.
Zhu SF
No affiliation info available
Zhou CY
No affiliation info available
Zhou QL
No affiliation info available

MeSH

AldehydesAlkenesAlkylationAlkynesCatalysisLigandsMolecular StructureNickelOrganometallic CompoundsOrganophosphorus CompoundsPropanolsSpiro CompoundsStereoisomerismZinc

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18834121

Citation

Yang, Yun, et al. "Nickel-catalyzed Enantioselective Alkylative Coupling of Alkynes and Aldehydes: Synthesis of Chiral Allylic Alcohols With Tetrasubstituted Olefins." Journal of the American Chemical Society, vol. 130, no. 43, 2008, pp. 14052-3.
Yang Y, Zhu SF, Zhou CY, et al. Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins. J Am Chem Soc. 2008;130(43):14052-3.
Yang, Y., Zhu, S. F., Zhou, C. Y., & Zhou, Q. L. (2008). Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins. Journal of the American Chemical Society, 130(43), 14052-3. https://doi.org/10.1021/ja805296k
Yang Y, et al. Nickel-catalyzed Enantioselective Alkylative Coupling of Alkynes and Aldehydes: Synthesis of Chiral Allylic Alcohols With Tetrasubstituted Olefins. J Am Chem Soc. 2008 Oct 29;130(43):14052-3. PubMed PMID: 18834121.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins. AU - Yang,Yun, AU - Zhu,Shou-Fei, AU - Zhou,Chang-Yue, AU - Zhou,Qi-Lin, Y1 - 2008/10/04/ PY - 2008/10/7/pubmed PY - 2009/1/29/medline PY - 2008/10/7/entrez SP - 14052 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 43 N2 - A highly efficient nickel-catalyzed asymmetric alkylative coupling of alkynes, aldehydes, and dimethylzinc has been realized by using bulky spirobiindane phosphoramidite ligands, affording allylic alcohols with a tetrasubstituted olefin functionality in high yields, high regioselectivities, and excellent enantioselectivities. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18834121/Nickel_catalyzed_enantioselective_alkylative_coupling_of_alkynes_and_aldehydes:_synthesis_of_chiral_allylic_alcohols_with_tetrasubstituted_olefins_ L2 - https://doi.org/10.1021/ja805296k DB - PRIME DP - Unbound Medicine ER -