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Synthesis 2019; 51(20): 3834-3846
DOI: 10.1055/s-0037-1611896
DOI: 10.1055/s-0037-1611896
paper
Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) (Discovery Grant DG-06438), the Canada Research Chairs program (227346), the Canada Foundation for Innovation (Leaders Opportunity Funds 227346), the Fonds de Recherche du Québec - Nature et Technologies (FRQNT Centre in Green Chemistry and Catalysis; RS-171310), and the Université de Montréal.Further Information
Publication History
Received: 26 June 2019
Accepted: 02 July 2019
Publication Date:
01 August 2019 (online)
Abstract
An enantioselective and non-oxidative methodology was developed to obtain enantioenriched cyclopropyl boronates using a diethanolamine-promoted selective decomplexation of dioxaborolane. The non-oxidative decomplexation of the dioxaborolane ligand from the cyclopropylmethoxide species formed in the dioxaborolane-mediated Simmons–Smith cyclopropanation reaction provided the enantioenriched CIDA-based (CIDA = N-cyclohexyliminodiacetic acid) borocyclopropane in 92% yield and 95.6:4.4 er. A robustness screen has shown diethanolamine to be compatible with esters, carbamates and N-heterocycles, providing a tool to access enantioenriched cyclopropanes carrying not only base-sensitive but oxidizable functional groups as well. Diethanolamine was found to be compatible with the modified zinco-cyclopropanation reaction of allyl alcohol to remove residual dioxaborolane from the corresponding cis-N-heterocycle cyclopropylmethanol, thereby leading to improved yields.
Key words
borocyclopropanes - heterocycles - Simmons–Smith reaction - zinco-cyclopropanation - cross-couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611896.
- Supporting Information
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For a related preparation of cyclopropane building blocks, see: