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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.6b00946 | DOI Listing |
Publication Analysis
Top Keywords
aldol reactions
8
sf5-enolates tiiv-mediated
4
tiiv-mediated aldol
4
reactions f···ti
4
f···ti bonding
4
bonding transition
4
transition structures
4
structures determines
4
determines high
4
high trans-
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!