Oxidative cyclisation of cinnamyl ethers mediated by CAN: a stereoselective synthesis of 3,4-trans disubstituted tetrahydrofuran derivatives

Abstract

The oxidative cyclisation of cinnamyl ethers mediated by cerium(IV) ammonium nitrate results in the stereospecific formation of 3,4-trans disubstituted tetrahydrofuran derivatives in moderate to good yields.

Recent Advances in Synthetic Transformations Mediated by Cerium(IV) Ammonium Nitrate

“…Thus, the reaction of trimethoxycinnamyl cinnamyl ether with CAN in methanol resulted in the stereoselective formation of the corresponding 3,4-trans-disubstituted tetrahydrofuran derivative in moderate yield. A marginal increase in the yield was noticed when the reaction was done under an oxygen atmosphere (Scheme ) 17 …”

Oxidative cyclization in the synthesis of 5‐ and 6‐membered N,O‐heterocycles

“…Along similar lines, CAN-mediated oxidative cyclization of cinnamyl ethers 352 and 354 gives SCHEME 76 SCHEME 77 rise to 3,4-trans-disubstituted THF derivatives 353 and 355, respectively, with a high stereospecificity (Scheme 80) [172].…”

Recent advances in CAN mediated reactions in organic synthesis

“…Under argon atmosphere, the reaction afforded the corresponding tetrahydrofuran derivatives as a mixture of methoxy and nitrato derivatives 71 and 72 in 2:1 ratio in high yields (Scheme 13). 82 It has been shown that homobenzylic ethers with pendant enolacetate moiety such as 73 can undergo highly efficient cleavage followed by 6-endo cyclization in the presence of CAN to afford tetrahydropyrone 74 with excellent stereocontrol. 83 5-endo Cyclization of enamide esters such as 75 in the presence of CAN led to disubstituted g-lactam 76 in moderate yields.…”