Oxidative intramolecular cyclization reactions of Cinnamayl ethers mediated by cerium (IV) ammonium nitrate (CAN): a stereoselective synthesis of 3,4-trans-disubstitutedtetrahydrofuran derivatives

Various alkoxy-cinnamyl cinnamyl ethers and an alkoxy-cinnamyl prenyl ether underwent stereoselective oxidative cyclizations on treatment with a methanolic solution of cerium(IV) ammonium nitrate to afford 3,4-trans- disubstituted tetrahydrofuran derivatives. Different products were obtained under aerobic and anaerobic conditions

Recent advances in synthetic transformations mediated by cerium(IV) ammonium nitrate

Cerium(IV) ammonium nitrate (CAN) has recently emerged as a versatile reagent for oxidative electron transfer; the overwhelming number of reports serve as a testimony to the unparalleled utility of CAN in a variety of transformations of synthetic importance. Our recent work has uncovered novel carbon-carbon bond-forming reactions leading to the one-pot synthesis of dihydrofurans, tetrahydrofurans, and aminotetralins. In addition, we have developed a number of facile carbon-heteroatom bond-forming reactions by the CAN-mediated oxidative addition of soft anions to alkenes. A mechanistic rationale has been provided for the reactions explored. As might be expected of very powerful one-electron oxidants, the chemistry of cerium(IV) oxidation of organic molecules is dominated by radical and radical cation chemistry

Oxidative addition of 1,3-dicarbonyl compounds to dienes mediated by CAN:Formation of dihydrofuran derivatives

352-356Oxidative addition of 1,3-dicarbonyl compounds to dienes constitutes a facile method for the synthesis of dihydrofuran derivatives

An exceedingly mild and efficient CAN mediated method for the deprotection of acetals

1234-1236<span style="font-size:12.0pt;font-family: " times="" new="" roman";mso-fareast-font-family:"times="" roman";mso-ansi-language:="" en-in;mso-fareast-language:en-in;mso-bidi-language:ar-sa"="" lang="EN-IN">An efficient and mild procedure for the deprotection of acetals using CAN(Cerium(IV) Ammonium Nitrate) has been described.</span

Novel dipolar cycloaddition reactions of zwitterionic species generated from dimethoxycarbene and dimethyl acetylenedicarboxylate with carbonyl compounds: facile synthesis of dihydrofuran derivatives

The reaction of 1:1 zwitterionic species, generated in situ by the addition of dimethoxycarbene to dimethyl acetylenedicarboxylate, towards carbonyl compounds is described. The reactions presented offer a one-pot synthesis of dihydrofuran and spiro dihydrofuran derivatives in high yields

A novel CAN-mediated oxidative rearrangement of monoterpenes

A facile CAN-mediated oxidative rearrangement of monoterpenes of the pinene family to afford bisamides and ether derivatives is described

A mild and efficient procedure for the preparation of dimethyl and diallyl acetals of aromatic aldehydes mediated by cerium(lV) ammonium nitrate

141-143The reaction of aromatic aldehydes with cerium(IV) ammonium nitrate (CAN) in alcohols to afford the corresponding acetals is described

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

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

CAN mediated cyclization of epoxypropyl cinnamyl ethers: a facile stereoselective synthesis of tetrahydropyran derivatives

Cerium(IV) ammonium nitrate in substoichiometric amounts, promotes the intramolecular cyclization of epoxypropyl cinnamyl ethers to the corresponding 3,4,5-trisubstituted tetrahydropyran derivatives in moderate to good yields

Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes

This Account focuses mainly on our recent endeavors in the area of multicomponent reactions (MCRs) involving zwitterionic species generated by the addition of isocyanides and nucleophilic carbenes such as dimethoxycarbene and N-heterocyclic carbenes to activated alkynes. The strategy employed encompasses the interception of 1:1 zwitterionic species, generated in situ with a wide range of electrophiles. The new MCRs developed offer an efficient and convenient entry into several heterocycles of biological and synthetic importance