Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2‑Propanol-Mediated Reductive Coupling

• Published in: Organic letters Vol. 20; no. 13; pp. 4144 - 4147
• Main Authors: Brito, Gilmar A, Della-Felice, Franco, Luo, Guoshun, Burns, Alexander S, Pilli, Ronaldo A, Rychnovsky, Scott D, Krische, Michael J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.07.2018; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; FUNCTIONALIZATION; ASYMMETRIC ALLYLATIONS; REAGENTS; ABSOLUTE-CONFIGURATION; STEREOSELECTIVITY; KINETIC RESOLUTION; CARBONYL ALLYLATION; PROPARGYLIC ALCOHOLS; ACETATE; OXIDATION LEVEL

Cyclometalated π-allyliridium C,O-benzoates modified by (S)-SEGPHOS or (S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSCCCHO. Absolute stereochemistries of the resulting secondary homoa...