TY - JOUR
T1 - Intramolecular reaction of oxo-substituted allenyl- and propargylstannane with aldehyde
AU - Kadota, Isao
AU - Hatakeyama, Daigo
AU - Seki, Katsura
AU - Yamamoto, Yoshinori
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 1996/4/22
Y1 - 1996/4/22
N2 - The Lewis acid mediated reactions of allenylstannanes 1 and 13 gave trans cyclic ethers 3a and 14, respectively, with high stereoselectivities. The cyclization to 7 gave trans cyclic ether 9a. The treatment of propargylstannanes 2 and 8 with Lewis acids such as SnCl4, BuSnCl3, and ZnCl2·OEt2 induced isomerization to allenylmetal species, which underwent cyclization to the corresponding 6- and 5-membered cyclic ethers 3 and 9, respectively. The stereoselectivities dependend upon the ring size and Lewis acid utilized.
AB - The Lewis acid mediated reactions of allenylstannanes 1 and 13 gave trans cyclic ethers 3a and 14, respectively, with high stereoselectivities. The cyclization to 7 gave trans cyclic ether 9a. The treatment of propargylstannanes 2 and 8 with Lewis acids such as SnCl4, BuSnCl3, and ZnCl2·OEt2 induced isomerization to allenylmetal species, which underwent cyclization to the corresponding 6- and 5-membered cyclic ethers 3 and 9, respectively. The stereoselectivities dependend upon the ring size and Lewis acid utilized.
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U2 - 10.1016/0040-4039(96)00469-8
DO - 10.1016/0040-4039(96)00469-8
M3 - Article
AN - SCOPUS:0029897844
SN - 0040-4039
VL - 37
SP - 3059
EP - 3062
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 17
ER -