Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS2 to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry