Gold-catalyzed three-component tandem process: an efficient and facile assembly of complex butenolides from alkynes, amines, and glyoxylic acid.
An efficient and facile gold-catalyzed three-component tandem process for the assembly of two types of highly functionalized butenolides has been developed. In this reaction system, more than four chemical bonds are formed by a single gold catalyst. The present tandem protocol includes a direct coupling of alkynes, amines, and glyoxylic acid and subsequent exclusively endo-selective cycloisomerization of alkynoic acids along with intermolecular electrophilic trapping; it utilizes three simple and commercially available starting materials to assemble architecturally complex and appealing butenolide scaffolds bearing other reactive sites for further manipulation.
Zhang
Qiang
Q
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China.
Cheng
Ming
M
Hu
Xiaoyu
X
Li
Bo-Gang
BG
Ji
Jian-Xin
JX
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006038:Glyoxylates / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*
D000480:Alkynes; D000588:Amines; D006038:Glyoxylates; D006046:Gold; C004511:butenolide; C031150:glyoxylic acid; D015107:4-Butyrolactone