Silver(I)-Catalyzed Diastereoselective Synthesis of anti-1,2-Hydroxyboronates.

Autor: Joannou MV; Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)., Moyer BS; Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)., Goldfogel MJ; Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA)., Meek SJ; Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290 (USA). sjmeek@unc.edu.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2015 Nov 16; Vol. 54 (47), pp. 14141-5. Date of Electronic Publication: 2015 Sep 25.
DOI: 10.1002/anie.201507171
Abstrakt: A catalytic protocol for the diastereoselective synthesis of anti-1,2-hydroxyboronates is described. The process provides access to secondary alkyl organoborons. The deborylative 1,2-addition reactions of alkyl 1,1-diborons proceed in the presence of a silver(I) salt with either KOtBu or nBuLi as an activator. The catalytic diastereoselective protocol can be extended to aryl, alkenyl, and alkyl aldehydes with up to 99:1 d.r.
(© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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