title: High chelation control of three contiguous stereogenic centers in the Reformatsky reactions of indium enolates with alpha-hydroxy ketones: unexpected stereochemistry of lactone formation.
abstract: [reaction: see text] A boat-type of chelated bicyclic transition state involving highly diastereoselective construction of three contiguous stereogenic centers in the Reformatsky reaction of indium enolates with alpha-alkoxy/hydroxy ketones is proposed. alpha-Hydroxy ketones with indium enolates furnished highly diastereoselective lactones, while alpha-alkoxy ketones gave acyclic esters in moderate selectivities. X-ray structure analyses of key products unequivocally revealed the unexpected stereochemistry of products and the reaction pathway.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Japan.
authors.forename: Srinivasarao Arulananda
authors.initials: SA
authors.lastname: Babu
authors.forename: Makoto
authors.initials: M
authors.lastname: Yasuda
authors.forename: Yuji
authors.initials: Y
authors.lastname: Okabe
authors.forename: Ikuya
authors.initials: I
authors.lastname: Shibata
authors.forename: Akio
authors.initials: A
authors.lastname: Baba