Yayınlanmış 1 Ocak 2017
| Sürüm v1
Dergi makalesi
Açık
Synthesis of 4-membered ring alkaloid analogues via intramolecular [2+2] cycloaddition involving keteniminium salt intermediates
Yazarlar/Oluşturanlar
- 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
Açıklama
We have developed a very straightforward method for the synthesis of 4-membered ring alkaloid analogues via intramolecular [2+2] cycloadditions. This involves the cyclization of a keteniminium salt in which an alkene is linked by the nitrogen atom, and where, the resulting cyclobutane iminium is reduced in a diastereoselective manner. Competition reactions have been performed to fully understand the features of this sequence. Moreover, DFT calculations have verified that the [2+2] cycloaddition step is driven by kinetic and not thermodynamic factors confirming all the experimental observations. (C) 2017 Elsevier Ltd. All rights reserved.
Dosyalar
bib-c1d4c6d5-db45-4a70-91c8-aa4d5938c442.txt
Dosyalar
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