TY - JOUR
T1 - Nickel-catalyzed regio- and enantioselective annulation reactions of 1,2,3,4-benzothiatriazine-1,1(2H)-dioxides with allenes
AU - Miura, Tomoya
AU - Yamauchi, Motoshi
AU - Kosaka, Akira
AU - Murakami, Masahiro
PY - 2010/7/5
Y1 - 2010/7/5
N2 - (Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline.
AB - (Figure Presented) Extrusion of N2:1,2,3,4-Benzothiatriazine1,1 (2H)-dioxides reacted with alienes in the presence of a nickel (0)/(R)-quinap complex to produce a variety of substituted 3,4-dihydro-1,2-benzothiazine1,1 (2H)-dioxides in a regio- and enantioselective fashion. An intermediate nickelacycle was generated through denitrogenative activation of the triazo moiety which allowed the intermolecular incorporation of an aliene group. quinap = 1-(2diphenylphosphino-1-naphthyl)isoquinoline.
KW - Annulation
KW - Asymmetric synthesis
KW - Nickel
KW - Nitrogen heterocycles
KW - Synthetic methods
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U2 - 10.1002/anie.201001918
DO - 10.1002/anie.201001918
M3 - Article
AN - SCOPUS:77954324811
SN - 1433-7851
VL - 49
SP - 4955
EP - 4957
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 29
ER -