title: Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis.
abstract: We describe the fully stereodivergent, dual catalytic α-allylation of linear aldehydes. The reaction proceeds via direct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter proved to be crucial for achieving high enantio- and diastereoselectivity (>99% ee, up to >20:1 dr). The utility of the method is demonstrated in a concise enantioselective synthesis of the antidepressant (-)-paroxetine.
authors: Eidgenössische Technische Hochschule Zürich , 8093 Zürich, Switzerland.
authors: Simon
authors: S
authors: Krautwald
authors: Michael A
authors: MA
authors: Schafroth
authors: David
authors: D
authors: Sarlah
authors: Erick M
authors: EM
authors: Carreira