Rh(I)-Catalyzed Regio- and Enantioselective Ring Opening of Vinyl Cyclopropanes.

Autor: Webster SJ; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Balázs LB; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Goetzke FW; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Stojalnikova V; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Liu K; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Christensen KE; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Mackenzie HW; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K., Fletcher SP; Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, U.K.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2024 Sep 04; Vol. 146 (35), pp. 24708-24715. Date of Electronic Publication: 2024 Aug 20.
DOI: 10.1021/jacs.4c09490
Abstrakt: We describe a Rh(I) catalyzed asymmetric ring opening of racemic vinyl cyclopropanes using aryl boronic acids as C-nucleophiles. When ferrocene-based chiral bisphosphines are used as ligands, the products are obtained with regioselectivities typically 99:1 r.r. and ee's generally between 88 and 96%. A wide range of aryl boronic acids can be used, and the products can be converted into a variety of targets. Preliminary mechanistic studies indicate that Zn(OTf) 2 plays a significant role in the reaction by promoting rhodium-ligand complex formation and accelerating the reaction. We expect this method and these mechanistic insights to be useful in the development of new asymmetric methods.
Databáze: MEDLINE
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