Palladium‐Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification1. (26th February 2015)

• Record Type: Journal Article
• Authors: Orcel, Ugo; Waser, Jerome
• Is Part Of: Angewandte Chemie. Volume 127:Number 17(2015)
• Page Start: 5339
• Page End: 5343
• Publication Date: 2015-02-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201500636
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Vicinal amino alcohols are important structural motifs of bioactive compounds. Reported herein is an efficient method for their synthesis based on the palladium‐catalyzed oxy‐alkynylation, oxy‐arylation, or oxy‐vinylation of allylic amines. High regio‐ and stereoselectivity were ensured through the in situ formation of a hemiaminal tether using the cheap commercially available trifluoroacetaldehyde in its hemiacetal form. The obtained compounds are important building blocks, which can be orthogonally deprotected to give either free alcohols, amines, or terminal alkynes.</p> </abstract>