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Diastereoselective Radical Hydrogen Transfer Reactions using N-Heterocyclic Carbene Boranes

Diastereoselective Radical Hydrogen Transfer Reactions using N-Heterocyclic Carbene Boranes

Journal of Organic Chemistry 81(22): 11427-11431

Reported herein are the first diastereoselective and Lewis acid-mediated radical reactions of N-heterocyclic carbene (NHC) boranes. We applied these reactions to the synthesis of four propionate diastereoisomers combining an aldol reaction, followed by a stereoselective radical-based reduction in which the NHC borane serves as the hydrogen donor, thus obviating the use of tin-based reagents. The 2,3-syn isomer is obtained by combining an NHC-borane and a Lewis acid (MgBr2·OEt2), while using a reverse polarity strategy provides the 2,3-anti isomer.

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Accession: 057614622

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PMID: 27709943

DOI: 10.1021/acs.joc.6b02066

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