窒素-アリール軸を基盤にした有機合成化学
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概要
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In this review, our recent studies in relation to synthetic organic chemistry based on the N-Ar axis, are embodied, which are divided by content into three sections as follows : (i) development of sufficiently chemoselective <I>N</I>-acylation reagents : a variety of storable <I>N</I>-acetyl-<I>N</I>- (2-trifluo-romethylphenyl) acetamide, <I>N</I>-benzoyl- (2-chlorophenyl) benzamide and <I>N</I>-acyl-<I>N</I>- (2, 3, 4, 5, 6-pentafluorophenyl) methanesufonamide, have been developed after systematic research on the structure-reactivity relationship and were found to serve as <I>N</I>-acylation reagents, exhibiting suffi-ciently better chemoselectivity compared with current <I>N</I>-acylation reagents; (ii) fundamental stud-ies of a chiral axis due to an acyclic imide-Ar Bond : the first example of optically active <I>N</I>-acyl-<I>N</I>- (<I>2</I>-t-butylphenyl) acetamide which possesses axial chirality based on an acyclic imide N-Ar bond rotation, has been found. Furthermore, the relationship between the stability to racemization and the steric and electronic effects, was elucidated; (iii) development of a chiral ligand possessing a N-Ar prochiral axis : our chiral ligand was designed on the following concept. As a chiral ligand design element for asymmetric transition metal catalyst, we use a “N-Ar prochiral axis”. Accordingly, though the N-Ar axis in our ligand is configurationally flexible, “prochiral”, the formation of the metal-our ligand complex should lead to a stable “chiral” N-Ar axis. And if this formation is largely reflected by the asymmetric center in the neighboring group, one of the two diastereomeric complexes due to the N-Ar axis, is expected to be selectively formed. Our synthesized ligands were evaluated with a standard palladium-catalyzed asymmetric allylic substitution and were found to exhibit high selectivity (up to 99% ee).
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