Vinyl Expoxide Tsuji Trost

Synthesis of highly functionalized allylic alcohols from vinyl oxiranes and n tosylhydrazones via a tsuji trost like palladium iodide catalyzed coupling.

Vinyl expoxide tsuji trost. A method where an allyl alcohol is formed from a tsuji trost allylation between a vinyl epoxide and an acyl containing nucleophile is described. Organic letters 2018 20 21 6891 6895. A method where an allyl alcohol is formed from a tsuji trost allylation between a vinyl epoxide and an acyl containing nucleophile is described. Subsequently a retro claisen condensation is utilized as a means of through space anion relay.

Palladium catalyzed substitution reactions of alkenyl epoxides christine courillon universite pierre et marie curie paris vi laboratoire de chimie organique de synthèse case 229 t. Palladium catalyzed cross coupling of vinyl epoxides and aziridines with organoboronic acids was performed by using 0 5 2 5 mol pincer complex catalyst. The tsuji trost reaction and related carbon carbon bond formation reactions. The tsuji trost reaction is the palladium catalyzed allylation of nucleophiles such as active methylenes enolates amines and phenols with allylic compounds such as allyl acetates and allyl bromides.

The reactions proceed under mild conditions affording allyl alcohols and amines with high regioselectivity and in good to excellent yields. The anion relay results in the formation of a reactive carbanion and simultaneously activates an allylic alcohol toward intramolecular tsuji trost. Trost reaction 22 vinyl epoxides have been employed previously in palla dium catalyzed allylations 23 but to the best of our knowl edge reports using anickel based catalyst a nonprecious inexpensive catalyst are scarce 24 with only afew examples being reported involving cycloaddition reactions atthe. Synthesis of vinyl cyclopropanes via anion relay cyclization.