Catalyst-controlled ring-opening cycloisomerization reactions of cyclopropenyl carboxylates for highly regioselective synthesis of different 2-alkoxyfurans.
Differently substituted 2-alkoxyfurans (2,3,4- or 2,3,5-trisubstituted furans) were highly regioselectively synthesized by means of the ring-opening cycloisomerization of the same cyclopropenyl carboxylates with good yields in different solvents and excellent regioselectivity by using [Cu(acac)(2)] (acac=acetylacetonate) or [RuCl(2)(PPh(3))(3)] as the catalyst, respectively. The structures of these two different types of furans were established by X-ray diffraction studies. A rationale has been proposed.
Chen
Jie
J
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P.R. China.
Ma
Shengming
S
D000438:Alcohols / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000438:Alcohols; D002264:Carboxylic Acids; D003521:Cyclopropanes; D005663:Furans; C059688:alkoxyl radical; D003300:Copper; C021985:cyclopropene; D012428:Ruthenium