Organocatalytic Highly Enantioselective Substitution of 3-(1-Tosylalkyl)indoles with Oxindoles Enables the First Total Synthesis of (+)-Trigolutes B.
A highly enantioselective organocatalytic substitution of 3-(1-tosylalkyl)indoles with oxindoles has been established by using chiral bifunctional organocatalysts, providing an efficient entry to multiply functionalized 3,3'-disubstituted oxindoles, and was exploited as the key step to enable the first asymmetric total synthesis of optically pure (+)-trigolutes B to be accomplished in a concise manner, within seven steps with an 18% overall yield.
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Jian-Zhou
JZ
Huang
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Chen-Long
CL
Zhang
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Yi-Fan
YF
Zhu
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Lu-Lu
LL
Li
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Dian-Feng
DF
Chen
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm.
Zhi-Yong
ZY
Han
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P. R. China), Fax: (+86) 551-360-6266 http://staff.ustc.edu.cn/∼gonglz/index.htm. gonglz@ustc.edu.cn.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) (P. R. China). gonglz@ustc.edu.cn.
Liu-Zhu
LZ
Gong
asymmetric⋅synthesis; enantioselectivity; organocatalysis; spirooxindoles; total synthesis