Gold(i)-catalyzed cascade cyclization of O-tethered 1,7-enynes bearing a cyclopropane moiety: construction of multi-substituted furans

Zang, Wenqing1; Wei, Yin1; Shi, Min1,2

2019-07-18

10.1039/c9cc03735g

CHEMICAL COMMUNICATIONS   影响因子和分区

1359-7345

1364-548X

A gold-catalyzed cascade cyclization of O-tethered 1,7-enynes bearing a cyclopropane moiety has been reported in this communication, affording multi-substituted furans in moderate to good yields. The reaction proceeded through an intramolecular O-nucleophilic addition and 3,3-sigmatropic rearrangement followed by ring-opening of the cyclopropane unit along with the further reaction with electrophiles. The C-C bond cleavage of a strained cyclopropane moiety in the presence of a gold catalyst and the aromatization provided the driving force for this cascade cyclization. The practical transformations of the obtained diiodinated furan have also been indicated.

SCI ; IC ; CCR ; EI

英语

NI期刊

通讯

National Natural Science Foundation of China[20472096] ; National Natural Science Foundation of China[21372241] ; National Natural Science Foundation of China[21572052] ; National Natural Science Foundation of China[20672127] ; National Natural Science Foundation of China[21421091] ; National Natural Science Foundation of China[21372250] ; National Natural Science Foundation of China[21121062] ; National Natural Science Foundation of China[21302203] ; National Natural Science Foundation of China[21772226] ; National Natural Science Foundation of China[20732008] ; National Natural Science Foundation of China[21772037] ; National Natural Science Foundation of China[21861132014]

Chemistry

Chemistry, Multidisciplinary

WOS:000475373500015

ROYAL SOC CHEMISTRY

CHEMISTRY

Web of Science

1.Univ Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth,Chinese Acad Sci, 345 Ling Ling Lu, Shanghai 200032, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Zang, Wenqing,Wei, Yin,Shi, Min. Gold(i)-catalyzed cascade cyclization of O-tethered 1,7-enynes bearing a cyclopropane moiety: construction of multi-substituted furans[J]. CHEMICAL COMMUNICATIONS,2019,55(56):8126-8129.

Zang, Wenqing,Wei, Yin,&Shi, Min.(2019).Gold(i)-catalyzed cascade cyclization of O-tethered 1,7-enynes bearing a cyclopropane moiety: construction of multi-substituted furans.CHEMICAL COMMUNICATIONS,55(56),8126-8129.

Zang, Wenqing,et al."Gold(i)-catalyzed cascade cyclization of O-tethered 1,7-enynes bearing a cyclopropane moiety: construction of multi-substituted furans".CHEMICAL COMMUNICATIONS 55.56(2019):8126-8129.