A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.
The gold(I)-catalyzed cycloisomerization of epoxy alkynes in the presence of a nucleophile is an efficient protocol to provide ketal skeletons with high stereoselectivity. An intramolecular reaction of propargylic/homopropargylic alcohols with oxirane to produce ketal/spiroketals in moderate yields under mild conditions has been reported. Moreover, the mechanism of this kind of reaction has been discussed on the basis of a series of control and (18)O tracer experiments.
Dai
Lun-Zhi
LZ
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, China.
Shi
Min
M
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry
D000480:Alkynes; D004852:Epoxy Compounds; D005663:Furans; D020005:Propanols; D013141:Spiro Compounds; C073812:2,3-dihydrofuran; D006046:Gold; C028255:propargyl alcohol; D005027:Ethylene Oxide