Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251978 | PMC |
| http://dx.doi.org/10.1002/anie.202017035 | DOI Listing |
Publication Analysis
Top Keywords
enantioselective alkoxycyclization
8
alkoxycyclization 16-enynes
8
total synthesis
8
16-enynes goldi-cavitands
4
goldi-cavitands total
4
synthesis mafaicheenamine
4
mafaicheenamine chiral
4
chiral goldi-cavitand
4
goldi-cavitand complexes
4
complexes developed
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!