Abstract
A catalytic, enantio-, and diastereoselective formation of sulfenyl acetals bearing multiple stereogenic centers is reported. Alkenyl aldehydes undergo a chiral thiiranium ion initiated cascade starting with intramolecular capture by a formyl group and termination by capture with HFIP solvent. This method provides a one-pot synthesis of dihydropyran and 1,3-disubstituted isochroman acetals in good to excellent yield and with high levels of diastereo- (up to >99:1 dr) and enantiocontrol (up to 99:1 er).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 12486-12490 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 58 |
| Issue number | 36 |
| DOIs | |
| State | Published - Sep 2 2019 |
Keywords
- Lewis base catalysis
- carbonyl nucleophiles
- isochromans
- sulfenoacetalization
- thiiranium ions
ASJC Scopus subject areas
- Catalysis
- General Chemistry