Palladium-catalyzed diastereoselective synthesis of homoaldol equivalent products. Issue 22 (31st May 2017)

• Record Type: Journal Article
• Authors: Horino, Yoshikazu; Sugata, Miki; Sugita, Tetsu; Aimono, Ataru; Abe, Hitoshi
• Is Part Of: Tetrahedron letters. Volume 58:Issue 22(2017)
• Page Start: 2131
• Page End: 2134
• Publication Date: 2017-05-31
• Subjects: Allylation -- Homoaldol equivalent reaction -- Palladium catalysis -- Allylpalladium; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.064
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Homoaldol equivalent products can be synthesized with high diastereoselectivity. Pd complex promotes isomerization of 1-alkenylboronates to generate allylboronates. Reaction involves allylboration of aldehydes with α-acetoxy allylboronates. Abstract: A palladium-catalyzed reaction of easily accessible 3-(pinacolatoboryl)allyl acetates and aldehydes provides facile access to synthetically useful homoaldol equivalent products with high diastereoselectivity. The reaction presumably proceeds via allylation of aldehydes with α-acetoxy allylboronates that produced in situ by reductive elimination from allylic gem -palladium/boryl intermediates.