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Asymmetric aziridination of 1,3‐dienes catalyzed by bisoxazoline‐copper complexes
Author(s) -
Ma Linge,
Du DaMing,
Xu Jiaxi
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20282
Subject(s) - aziridine , chemistry , nitrene , regioselectivity , chirality (physics) , catalysis , axial chirality , copper , organic chemistry , medicinal chemistry , stereochemistry , enantioselective synthesis , combinatorial chemistry , ring (chemistry) , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
The asymmetric aziridination of 1,3‐dienes catalyzed by bisoxazoline‐CuOTf complexes with PhINTs as a nitrene precursor has been achieved in moderate yields with up to >99:1 regioselectivity, up to >99% diastereoselectivity, and up to 80% enantioselectivity. α,β,γ,δ‐Unsaturated ketones usually produced cis ‐γ,δ‐aziridinated products, while 1,4‐diphenyl‐1,3‐butadiene afforded both of cis ‐ and trans ‐aziridine derivatives as major products by the use of different bisoxazoline ligands. The configuration of cis ‐aziridine derivatives was proposed on the basis of the reaction mechanism. Chirality, 2006. © 2006 Wiley‐Liss, Inc.