Synthesis of new substituted 7,12-dihydro-6,12-methanodibenzo[c,f]azocine-5-carboxylic acids containing a tetracyclic tetrahydroisoquinoline core structure

A convenient and simple protocol has been developed for the synthesis of a series of new tetracyclic tetrahydroisoquinoline derivatives, 7,12-dihydro-6,12-methanodibenzo[c,f]-azocine-5-carboxylic acids by three component Petasis reaction with the use of aminoacetaldehyde acetals bearing substituted benzyl groups as the amine components followed by Pomeranz–Fritsch double cyclization reaction. By applying this method, several acids have been prepared in satisfactory yields. An unprecedented chemical behavior of a Petasis reaction product in diluted HCl solution leading to the formation of a phenylglycine derivative has been observed and the mechanism explaining such reactivity has been proposed.

Asymmetric Petasis reaction for the synthesis of chiral α- and β-butadienyl amines

Chiral α- and β-butadienyl amines are both available via the asymmetric Petasis reaction of pinacol homoallenyl- and isoprenylboronates.

A Metal-free Petasis reaction towards the synthesis of N-(-substituted)alkyl sulfoximines/sulfonimidamides

Herein, we disclose a metal-free novel approach for the synthesis of N-( -substituted)alkyl sulfoximines/sulfonimidamides via one-pot multicomponent Petasis reactions of aryl boronic acids, ortho-hydroxyarylaldehydes and sulfoximines/sulfonimidamides in moderate to very...