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Stereoselective Cyclopropanation of 1,1-Diborylalkenes via Palladium-Catalyzed (Trimethylsilyl)diazomethane Insertion

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卷 24, 期 27, 页码 4949-4953

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01885

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  1. Ministerio de Econom?a y Competitividad y por el Fondo Europeo de Desarrollo Regional FEDER [PID2019-109674GB-I00]

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Palladium catalysis enables the cyclopropanation of 2-substituted 1,1-diborylalkenes with (trimethylsilyl)diazomethane, controlling the relative stereoselectivity. Furthermore, further reactions involving chiral boryl motifs lead to the formation of polyfunctional cycloopropyl alcohols with controlled enantioselectivity.
Palladium catalyzes the cydclopropanation of 2-substituted 1,1-diborylalkenes with (trimethylsilyl)diazomethane. The relative stereoselectivity is controlled via a carbene insertion sequence generating an exclusive anti conformation between the R and SiMe3 substituents. Mixed 1,1-diborylalkenes also contributed to the formation of stereoselective B, B, Si-cyclopropanes. Orthogonal activation with (NaOBu)-Bu-t gives protodeborylation preferentially on the boron moiety syn to the aryl group. Further oxidation gives access to polyfunctional cycloopropyl alcohols with controlled enantioselectivity when chiral boryl motifs are involved.

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