Premium
Palladium‐Catalyzed Vicinal Amino Alcohols Synthesis from Allyl Amines by In Situ Tether Formation and Carboetherification
Author(s) -
Orcel Ugo,
Waser Jerome
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500636
Subject(s) - chemistry , hemiaminal , vicinal , palladium , allylic rearrangement , stereoselectivity , aminolysis , catalysis , in situ , combinatorial chemistry , organic synthesis , organic chemistry
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.