En Route to Diastereopure Polycyclic γ-Lactones by
Iridium-Catalyzed Hydride Transfer
Yang Chen, Jingyu Zhang, Yecheng Wang, Hongguang Du, Jiaxi Xu and
Zhanhui Yang*
Chin. J. Chem.2023, 41, XXX—XXX. DOI:
10.1002/cjoc.202300XXX
An iridium-catalyzed highly diastereoselective and efficient route to
diastereopure bi- and polycyclic γ-lactones is achieved, featuring high
levels of stereocontrol, broad substrate scope, and high catalyst
efficiency (S/C up to 5000). The large steric hindrance of the
iridium hydride species and the intramolecular hydrogen bonding underlie
the success of the highly diastereoselective reductive lactonization. A
general empirical rule based on facial selectivity analysis is proposed
for explaining and predicting the stereochemistry.