Published January 1, 2016
| Version v1
Journal article
Open
New access to quaternary aminocyclobutanes via nucleophilic addition on cyclobutaniminium salts
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 the first [2+2] cycloaddition between a keteniminium salt and an alkene followed by a nucleophilic addition on the in situ generated cyclobuteniminium salts. This one-pot sequence enables the formation of quaternary centers with high level of stereoselectivity and is largely applicable to the synthesis of highly strained intermediates as well as precursor for spirohydantoins. Moreover, DFT calculations support deuterated experiments showing that no spontaneous iminium-enamine tautomerization can exist during the [2+2] cycloaddition process. (C) 2016 Elsevier Ltd. All rights reserved.
Files
bib-aacbcec4-e049-4626-bb32-5f0170bbc3f8.txt
Files
(232 Bytes)
| Name | Size | Download all |
|---|---|---|
|
md5:18c147e57f37f199738d99f295567252
|
232 Bytes | Preview Download |