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Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane.
J Am Chem Soc. 2017 05 17; 139(19):6526-6529.JA

Abstract

We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac)2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86%-99% ee).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Yu S
Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543, Singapore.
Wu C
Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543, Singapore.
Ge S
Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543, Singapore.

MeSH

AlkynesBoranesBoron CompoundsCatalysisCobaltCyclizationLigandsMolecular Structure

Pub Type(s)

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

Language

eng

PubMed ID

28449577

Citation

Yu, Songjie, et al. "Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes With Pinacolborane." Journal of the American Chemical Society, vol. 139, no. 19, 2017, pp. 6526-6529.
Yu S, Wu C, Ge S. Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane. J Am Chem Soc. 2017;139(19):6526-6529.
Yu, S., Wu, C., & Ge, S. (2017). Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane. Journal of the American Chemical Society, 139(19), 6526-6529. https://doi.org/10.1021/jacs.7b01708
Yu S, Wu C, Ge S. Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes With Pinacolborane. J Am Chem Soc. 2017 05 17;139(19):6526-6529. PubMed PMID: 28449577.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane. AU - Yu,Songjie, AU - Wu,Caizhi, AU - Ge,Shaozhong, Y1 - 2017/05/04/ PY - 2017/4/30/pubmed PY - 2018/5/25/medline PY - 2017/4/29/entrez SP - 6526 EP - 6529 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 139 IS - 19 N2 - We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac)2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen-, and carbon-tethered 1,6-enynes underwent this asymmetric transformation, yielding both alkyl- and vinyl-substituted boronate esters containing chiral tetrahydrofuran, cyclopentane, and pyrrolidine moieties with high to excellent enantioselectivities (86%-99% ee). SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/28449577/Cobalt_Catalyzed_Asymmetric_Hydroboration/Cyclization_of_16_Enynes_with_Pinacolborane_ L2 - https://doi.org/10.1021/jacs.7b01708 DB - PRIME DP - Unbound Medicine ER -