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. 2015 Nov 16;54(47):14141-5.
doi: 10.1002/anie.201507171. Epub 2015 Sep 25.

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

Matthew V Joannou  1 , Brandon S Moyer  1 , Matthew J Goldfogel  1 , Simon J Meek  2
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Silver(I)-Catalyzed Diastereoselective Synthesis of anti-1,2-Hydroxyboronates

Matthew V Joannou et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: alcohols; asymmetric catalysis; boron; diastereoselectivity; silver.

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