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Strategic Trimethylsilyldiazomethane Insertion into pinB–SR Followed by Selective Alkylations

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Department Química Física i Inorgànica University Rovira i Virgili, C/Marcel·lí Domingo s/n, Tarragona 43007, Spain
Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick E4L 1G8, Canada
Cite this: Org. Lett. 2016, 18, 15, 3830–3833
Publication Date (Web):July 26, 2016
https://doi.org/10.1021/acs.orglett.6b01840
Copyright © 2016 American Chemical Society

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    Abstract

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    The insertion of the diazo derivative Me3SiCHN2 into pinB–SR σ bonds (R = Ph, Tol, Bn) allows a direct synthesis of multisubstituted H–C(SR)(Bpin)(SiMe3) compounds. Consecutive base-assisted transformations of HC(S)(B) (Si) systems lead to deborylative alkylations, Sommelet–Haüser rearrangements, and deprotoalkylations. Intramolecular cyclizations can be selectively performed either via desilylative or deborylative manifolds by fine-tuning the base employed.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b01840.

    • Experimental procedures and spectral data for insertion of Me3SiCHN2 into pinB-SR, deborylative alkylation, selective protodesilylation, deprotonation/alkylation, deborylative cyclization, and desilylative cyclization (PDF)

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    18. Enrico La Cascia, Ana B. Cuenca, Elena Fernández. Opportune gem ‐Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins. Chemistry – A European Journal 2016, 22 (52) , 18737-18741. https://doi.org/10.1002/chem.201604782
    19. Marc G. Civit, Jordi Royes, Christopher M. Vogels, Stephen A. Westcott, Ana B. Cuenca, Elena Fernandez. ChemInform Abstract: Strategic Trimethylsilyldiazomethane Insertion into pinB—SR Followed by Selective Alkylations.. ChemInform 2016, 47 (52) https://doi.org/10.1002/chin.201652079

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