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Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers.
Angew Chem Int Ed Engl. 2022 07 18; 61(29):e202117413.AC

Abstract

Catalytic asymmetric hydroboration of alkenes is a powerful tool for the synthesis of natural products, agrochemicals, and pharmaceuticals via the versatile transformations of chiral alkyl boronic esters. However, the scope of available alkenes is limited to styrenes, activated alkenes, and compounds with directing groups. The catalytic enantioselective hydroboration of heteroatom-substituted alkenes is rarely explored and those catalyzed by earth-abundant metals are yet to be reported. Herein, we report a cobalt-catalyzed asymmetric hydroboration of ketone-derived silyl enol ethers and provide a convenient approach to access valuable enantiopure β-hydroxy boronic esters. This protocol features mild reaction conditions, a broad substrate scope, and excellent enantioselectivities (up to 99 % ee). This approach was applied in the successful synthesis of salmeterol and albuterol, demonstrating its potential to streamline complex molecule synthesis.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Dong W
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.
Ye Z
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.
Zhao W
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.

MeSH

AlcoholsAlkenesCatalysisCobaltEstersEthersKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

35488385

Citation

Dong, Wenke, et al. "Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers." Angewandte Chemie (International Ed. in English), vol. 61, no. 29, 2022, pp. e202117413.
Dong W, Ye Z, Zhao W. Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers. Angew Chem Int Ed Engl. 2022;61(29):e202117413.
Dong, W., Ye, Z., & Zhao, W. (2022). Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers. Angewandte Chemie (International Ed. in English), 61(29), e202117413. https://doi.org/10.1002/anie.202117413
Dong W, Ye Z, Zhao W. Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers. Angew Chem Int Ed Engl. 2022 07 18;61(29):e202117413. PubMed PMID: 35488385.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Cobalt-Catalyzed Hydroboration of Ketone-Derived Silyl Enol Ethers. AU - Dong,Wenke, AU - Ye,Zhiyang, AU - Zhao,Wanxiang, Y1 - 2022/05/26/ PY - 2021/12/21/received PY - 2022/5/1/pubmed PY - 2022/7/14/medline PY - 2022/4/30/entrez KW - Asymmetric Catalysis KW - Cobalt KW - Hydroboration KW - Organoboronates KW - Silyl Enol Ethers SP - e202117413 EP - e202117413 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 61 IS - 29 N2 - Catalytic asymmetric hydroboration of alkenes is a powerful tool for the synthesis of natural products, agrochemicals, and pharmaceuticals via the versatile transformations of chiral alkyl boronic esters. However, the scope of available alkenes is limited to styrenes, activated alkenes, and compounds with directing groups. The catalytic enantioselective hydroboration of heteroatom-substituted alkenes is rarely explored and those catalyzed by earth-abundant metals are yet to be reported. Herein, we report a cobalt-catalyzed asymmetric hydroboration of ketone-derived silyl enol ethers and provide a convenient approach to access valuable enantiopure β-hydroxy boronic esters. This protocol features mild reaction conditions, a broad substrate scope, and excellent enantioselectivities (up to 99 % ee). This approach was applied in the successful synthesis of salmeterol and albuterol, demonstrating its potential to streamline complex molecule synthesis. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/35488385/Enantioselective_Cobalt_Catalyzed_Hydroboration_of_Ketone_Derived_Silyl_Enol_Ethers_ DB - PRIME DP - Unbound Medicine ER -