Transfer of Chirality in Rhodium-Catalyzed Intramolecular (5+2) Cycloaddition of 3-Acyloxy-14-enyne (ACE) and Alkyne: Enantioselective Synthesis of Bicyclo5.3.0decatrienes

摘要

Chiral BicyclicBicyclo[5.3.0]decatrienes were prepared enantioselectively for the first time from readily available chiral 3-acyloxy-1,4-enynes (ACEs). The chirality of the allylic/propargylic esters in ACEs could be transferred with high efficiency to the bicyclic products in most cases. The experimentally observed overall inversion of stereochemistry confirmed the prediction from previous computational studies.