844857-48-3

Upstream product

• 953780-89-7 (Z,Z)-trifluoromethanesulfonic acid 2-[2-hydroxy-5-phenyl-2-(3-phenyl-2-propenyl)-4-pentenyl]phenyl ester 
• 953780-77-3 2-[1-hydroxy-4-phenyl-1-(3-phenyl-2-propynyl)-3-butynyl]phenol 
• 953780-74-0 2-[1-hydroxy-1-(2-propynyl)-3-butynyl]phenol 
• 844857-41-6 2-[1-hydroxy-4-trimethylsilyl-1-(3-trimethylsilyl-2-propynyl)-3-butynyl]phenol 

Downstream Products

• 844857-51-8 (R,E,E)-4-benzylidene-2-(3-phenyl-2-propenyl)-1,2,3,4-tetrahydro-2-naphthalenol 
• 953780-84-2 trifluoromethansulfonic acid (E,E)-2-[2-methoxy-5-phenyl-2-(3-phenyl-2-propenyl)-4-pentenyl]phenyl ester 

Relevant academic research and scientific papers

Oxygen donor-mediated equilibration of diastereomeric alkene-palladium(II) intermediates in enantioselective desymmetrizing heck cyclizations

This investigation examines the origin of enantioselection in the desymmetrization of an acyclic prochiral Heck cyclization precursor. High asymmetric induction (97-98% ee) is attributed to a temporary interaction of a Lewis basic oxygen donor with weakly Lewis acidic palladium(II). A series of control experiments combined with quantum-chemical model calculations provided sound evidence for a mechanism involving oxygen donor-mediated, rapid equilibration of diastereomeric alkene-palladium(II) complexes prior to the selectivity-determining ring-closing event, a Curtin-Hammett scenario. Our study also highlights the importance of the cationic pathway (triflate counter anions versus halido ligand) and alkene stereochemistry (E versus Z) in asymmetric Heck reactions.