TY - JOUR
T1 - Nitrosoallene-Mediated endo-Cyclizations for the Synthesis of (Hetero)cyclic α-Substituted exo-Unsaturated Oximes
AU - Tanimoto, Hiroki
AU - Ueda, Sho
AU - Morimoto, Tsumoru
AU - Kakiuchi, Kiyomi
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/2/2
Y1 - 2018/2/2
N2 - Nitrosoallene-mediated endo-dig cyclization reactions producing (hetero)cyclic exo-unsaturated oximes (enoximes) are described. The intramolecular 1,4-type addition to in situ generated nitrosoallenes afforded α-substituted cyclic enoximes with exo-methylene units, which are the favored conformation for further cyclizations. The strong electron-withdrawing ability of the nitroso group facilitated the construction of five-to-seven-membered ring systems via C-O, C-N, C-S, and C-C bond formations, including a quaternary carbon center, at low temperatures.
AB - Nitrosoallene-mediated endo-dig cyclization reactions producing (hetero)cyclic exo-unsaturated oximes (enoximes) are described. The intramolecular 1,4-type addition to in situ generated nitrosoallenes afforded α-substituted cyclic enoximes with exo-methylene units, which are the favored conformation for further cyclizations. The strong electron-withdrawing ability of the nitroso group facilitated the construction of five-to-seven-membered ring systems via C-O, C-N, C-S, and C-C bond formations, including a quaternary carbon center, at low temperatures.
UR - http://www.scopus.com/inward/record.url?scp=85041555919&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b02936
DO - 10.1021/acs.joc.7b02936
M3 - 学術論文
C2 - 29336557
AN - SCOPUS:85041555919
SN - 0022-3263
VL - 83
SP - 1614
EP - 1626
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -