Ponomarenko, Maksym V.; Grabowsky, Simon; Pal, Rumpa; Röschenthaler, Gerd-Volker; Fokin, Andrey A. (2016). SF5 -Enolates in Ti(IV)-Mediated Aldol Reactions. Journal of organic chemistry, 81(15), pp. 6783-6791. American Chemical Society 10.1021/acs.joc.6b00946
![[img]](https://boris.unibe.ch/style/images/fileicons/text.png) |
Text
036_Ponomarenko2016_JOrgChem.pdf - Published Version Restricted to registered users only Available under License Publisher holds Copyright. Download (1MB) |
The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2. Such bonding is canceled in nucleophilic solvents where opposite cis-stereochemistry is observed. The potential of thus obtained stereoisomeric SF5-aryl acrylates as dipolarophiles in the preparation of SF5-containing heterocycles is demonstrated.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Grabowsky, Simon |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
0022-3263 |
Publisher: |
American Chemical Society |
Language: |
English |
Submitter: |
Simon Grabowsky |
Date Deposited: |
06 Feb 2020 11:21 |
Last Modified: |
05 Dec 2022 15:35 |
Publisher DOI: |
10.1021/acs.joc.6b00946 |
BORIS DOI: |
10.7892/boris.138458 |
URI: |
https://boris.unibe.ch/id/eprint/138458 |
Actions (login required)
 |
Edit item |