Stereospecific Nickel-Catalyzed Borylation of Secondary Benzyl Pivalates

Abstract A stereoselective nickel-catalyzed direct borylation of enantioenriched secondary benzyl pivalates is described. This methodology is characterized by an intriguing cooperativity of simple nickel and copper salts to promote the targeted C–B bond formation under mild reaction conditions. Unli...

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Bibliographic Details
Published in:Synlett 2017-12, Vol.28 (19), p.2604-2608
Main Authors: Martin-Montero, R., Krolikowski, T., Zarate, C., Manzano, R., Martin, R.
Format: Article
Language:English
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cluster
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Summary:Abstract A stereoselective nickel-catalyzed direct borylation of enantioenriched secondary benzyl pivalates is described. This methodology is characterized by an intriguing cooperativity of simple nickel and copper salts to promote the targeted C–B bond formation under mild reaction conditions. Unlike classical S N 2-type processes, this protocol occurs with a neat retention of configuration, resulting in synthetically versatile benzyl boronic esters with excellent stereochemical fidelity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1590962