Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols

Author:

Siddiqui Saher H.,Navuluri Chandrasekhar,Charette André B.1ORCID

Affiliation:

1. FRQNT Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal

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.

Funder

Natural Sciences and Engineering Research Council of Canada

Canada Research Chairs

Canada Foundation for Innovation

Fonds de Recherche du Québec - Nature et Technologies

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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