Ring-Opening 1-Amino-3-aminomethylation of Donor-Acceptor Cyclopropanes via 1,3-Diazepanes

Lennart K B Garve; Peter G Jones; Daniel B Werz

doi:10.1002/anie.201704619

Ring-Opening 1-Amino-3-aminomethylation of Donor-Acceptor Cyclopropanes via 1,3-Diazepanes

Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9226-9230. doi: 10.1002/anie.201704619. Epub 2017 Jun 28.

Authors

Lennart K B Garve¹, Peter G Jones², Daniel B Werz¹

Affiliations

¹ Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106, Braunschweig, Germany.
² Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106, Braunschweig, Germany.

PMID: 28598583
DOI: 10.1002/anie.201704619

Abstract

The first ring-opening reaction of donor-acceptor cyclopropanes to give diamines is reported. For this reaction, a 1,3-bisfunctionalization was developed using cyclopropanes, triazinanes, and Sc(OTf)₃ as the catalyst, followed by treatment with acid. The reaction proceeds under very mild conditions and tolerates many functional groups. Moreover, a library of various 1,3-diazepanes, which arise as intermediates of the first formal aza-[4+3]-cycloaddition reaction with donor-acceptor cyclopropanes, was synthesized.

Keywords: 1,3-bisfunctionalization; [4+3]-cycloaddition; cyclopropanes; donor-acceptor compounds; ring-opening reactions.

Publication types

Research Support, Non-U.S. Gov't