Premium
Copper Promoted Oxidative Coupling of SnAP Hydrazines and Aldehydes to Form Chiral 1,4,5‐Oxadiazepanes and 1,2,5‐Triazepanes
Author(s) -
Luescher Michael U.,
Songsichan Teerawat,
Hsieh ShengYing,
Bode Jeffrey W.
Publication year - 2017
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201700199
Subject(s) - chemistry , hydrazine (antidepressant) , reagent , oxidative phosphorylation , oxidative coupling of methane , amine gas treating , copper , tin , combinatorial chemistry , organic chemistry , catalysis , biochemistry , chromatography
SnAP (Sn (tin) amine protocol) hydrazine reagents and aldehydes undergo oxidative, copper mediated coupling to form substituted 1,4,5‐oxadiazepanes and 1,2,5‐triazepanes. Unlike all prior reactions involving SnAP reagents, the SnAP hydrazine reagents undergo a molecular oxygen‐assisted oxidative cyclization. The air‐ and moisture tolerant transformation accommodates a broad range of groups including electron‐rich, electron‐poor aromatic, heteroaromatic, and aliphatic aldehydes and is amenable to gram scale synthesis. These unusual, chiral heterocycles have unexpectedly large optical rotations, which may find use in optical materials.