title: The Z-enoate assisted, Meyer-Schuster rearrangement cascade: unconventional synthesis of α-arylenone esters.
abstract: Brønsted acid promoted nucleophilation of propargylic alcohols during the Meyer-Schuster rearrangement (M-S) has been introduced. A novel concept of reverse polarization of the M-S intermediate allenyl cation has been realized by employing a cis-enoate assisted strategy. This idea is well demonstrated by the metal free synthesis of complex, highly functionalized cyclic as well as acyclic α-arylenones. The synthetic importance of the derived products was highlighted by the efficient conversion to biologically relevant molecules such as pyrazoles and 4,5-seco-abietane.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamilnadu, India. beeru@iitm.ac.in.
authors.forename: Prabhakararao
authors.initials: P
authors.lastname: Tharra
authors.affiliation: Department of Chemistry, Indian Institute of Technology Madras, Chennai-600036, Tamilnadu, India. beeru@iitm.ac.in.
authors.forename: Beeraiah
authors.initials: B
authors.lastname: Baire