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Domino Synthesis of α,β‐Unsaturated γ‐Lactams by Stereoselective Amination of α‐Tertiary Allylic Alcohols
Author(s) -
Xie Jianing,
Xue Sijing,
EscuderoAdán Eduardo C.,
Kleij Arjan W.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810160
Subject(s) - allylic rearrangement , stereoselectivity , chemistry , domino , amination , catalysis , substrate (aquarium) , functional group , combinatorial chemistry , palladium , organic chemistry , polymer , oceanography , geology
Tertiary allylic alcohols equipped with a carboxyl group can be smoothly aminated under ambient conditions by a conceptually new and stereoselective protocol under palladium catalysis. The in situ formed Z‐configured γ‐amino acid cyclizes to afford an α,β‐unsaturated γ‐lactam, releasing water as the only byproduct. This practical catalytic transformation highlights the use of a carboxyl group acting as an activating and stereodirecting functional group to provide a wide series of pharma‐relevant building blocks. Various control reactions support the crucial role of the carboxyl group in the substrate to mediate these transformations.