Enantioselective Synthesis of cis- and trans-Borocyclopropylmethanol: Simple Building Blocks To Access Heterocycle-Substituted Cyclopropylmethanols
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Published:2019-08-01
Issue:20
Volume:51
Page:3834-3846
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ISSN:0039-7881
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Container-title:Synthesis
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language:en
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Short-container-title:Synthesis
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
Cited by
1 articles.
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