Premium
Palladium‐Catalyzed Three‐Component Reaction of 3‐(Tri‐ n ‐ butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ‐Substituted Allylic Tin Reagents
Author(s) -
Horino Yoshikazu,
Sugata Miki,
Abe Hitoshi
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201501049
Subject(s) - chemistry , allylic rearrangement , palladium , aldehyde , xantphos , catalysis , alkene , medicinal chemistry , reagent , organic chemistry
A three‐component reaction of 3‐(tri‐ n ‐butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium‐Xantphos catalyst system predominately gave ( E )‐ anti ‐homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem ‐palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in‐situ ‐generated ( E )‐vinylpalladium acetate with the triorganoborane.