Published January 1, 2016
| Version v1
Journal article
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Synthesis of amino-cyclobutanes via [2+2] cycloadditions involving keteniminium intermediates
Creators
- 1. Syngenta Crop Protect AG, Crop Protect Res, Res Chem, Schaffhauserstr 101, CH-4332 Basel, Switzerland
- 2. Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey
Description
We describe an efficient method for the synthesis of aminocyclobutanes via a [2 + 2] cycloaddition between a keteniminium salt and an alkene, followed by a reduction step. The use of easily removable N-allyl moieties as protecting groups increases the potential of this method to access, in a few steps, highly functionalized cyclobutaneamine-containing building blocks. Moreover, DFT calculations verify the compatibility of N-allyl and N-propargyl keteniminiums in [2 + 2] cycloaddition reactions. (C) 2016 Elsevier Ltd. All rights reserved.
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