TY - JOUR
T1 - Enantioselective construction of 2,3-dihydrofuro[2,3-b]quinolines through supramolecular hydrogen bonding interactions
AU - Zhong, Fangrui
AU - Bach, Thorsten
N1 - Publisher Copyright:
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2014/10/13
Y1 - 2014/10/13
N2 - The first asymmetric synthesis of 2,3-dihydrofuro[2,3-b]quinolines has been achieved by a cascade asymmetric aziridination/intramolecular ring-opening process of differently substituted 3-alkenylquinolones. Good yields and high enantioselectivities (up to 78% yield and 95% ee) were recorded when employing 2,2,2-trichloroethoxysulfonamide as the nitrene source, PhI(OCOtBu)2 as the oxidant, and a chiral C2 -symmetric Rh(II) complex as the catalyst (1 mol%). The catalyst bears two lactam motifs, which serve as binding sites for substrate coordination through supramolecular hydrogen-bonding interactions.
AB - The first asymmetric synthesis of 2,3-dihydrofuro[2,3-b]quinolines has been achieved by a cascade asymmetric aziridination/intramolecular ring-opening process of differently substituted 3-alkenylquinolones. Good yields and high enantioselectivities (up to 78% yield and 95% ee) were recorded when employing 2,2,2-trichloroethoxysulfonamide as the nitrene source, PhI(OCOtBu)2 as the oxidant, and a chiral C2 -symmetric Rh(II) complex as the catalyst (1 mol%). The catalyst bears two lactam motifs, which serve as binding sites for substrate coordination through supramolecular hydrogen-bonding interactions.
KW - asymmetric catalysis
KW - enantioselectivity
KW - hydrogen bonding
KW - nitrogen heterocycles
KW - rhodium
UR - http://www.scopus.com/inward/record.url?scp=84930510362&partnerID=8YFLogxK
U2 - 10.1002/chem.201404617
DO - 10.1002/chem.201404617
M3 - Article
C2 - 25196199
AN - SCOPUS:84930510362
SN - 0947-6539
VL - 20
SP - 13522
EP - 13526
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 42
ER -