A novel Prins cyclization through benzylic/allylic C-H activation.
A step-economic method to construct the tetrahydropyran ring, involving sequential benzylic/allylic C-H bond activation via DDQ oxidation and nucleophilic attack of an unactivated olefin, is described. The equatorial-trisubstituted Prins products are obtained from benzyl and allyl homoallylic ethers with high yield and stereochemical fidelity.
Yu
Binxun
B
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, 730000, PR China.
Jiang
Tuo
T
Li
Junpeng
J
Su
Yingpeng
Y
Pan
Xinfu
X
She
Xuegong
X
D003500:Cyclization; D003516:Cycloparaffins / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D008752:Methylene Chloride / Q000737:chemistry; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
D003516:Cycloparaffins; D004987:Ethers; D011714:Pyrans; D008752:Methylene Chloride