Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521026 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.3c02302 | DOI Listing |
Publication Analysis
Top Keywords
addition dialkyl
8
dialkyl malonates
8
malonates β-arylethenesulfonyl
8
β-arylethenesulfonyl fluorides
8
high-pressure conditions
8
enantioselective addition
4
fluorides high-pressure
4
conditions application
4
application high-pressure
4
conditions enables
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!