Premium
Kinetic Resolution of Secondary Allyl Boronates and Their Application in the Synthesis of Homoallylic Amines
Author(s) -
Villar Laura,
Orlov Nikolai V.,
Kondratyev Nikolay S.,
Uria Uxue,
Vicario Jose L.,
Malkov Andrei V.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804395
Subject(s) - chemistry , reagent , kinetic resolution , stereoselectivity , chirality (physics) , double bond , resolution (logic) , organic chemistry , boron , combinatorial chemistry , enantioselective synthesis , catalysis , chiral symmetry , physics , quantum mechanics , artificial intelligence , quark , computer science , nambu–jona lasinio model
Abstract Highly enantioenriched, chromatographically‐stable secondary allyl boronates featuring a 1,1,2,2‐tetraethyl‐1,2‐ethanediol fragment (Epin) were obtained by kinetic resolution of their racemic mixtures. The Epin group at boron considerably improved stability of allyl boronates allowing them to be readily isolated by chromatography on silica. The resolved reagents were applied in stereoselective synthesis of homoallylic amines with an internal double bond employing unprotected imines formed in situ from aldehydes and ammonia. The reactions proceeded with an excellent transfer of chirality.