Silver(I)‐Catalyzed Diastereoselective Synthesis of anti‐1,2‐Hydroxyboronates |
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| Authors: | Matthew V. Joannou Brandon S. Moyer Matthew J. Goldfogel Prof. Simon J. Meek |
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| Affiliation: | Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, NC 27599‐3290 (USA) |
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| 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. |
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| Keywords: | alcohols asymmetric catalysis boron diastereoselectivity silver |
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