title: Grignard reactions of 4-substituted-2-keto-1,3-dioxanes: highly diastereoselective additions controlled by a remote alkyl group.
abstract: [see reaction]. The reactions of Grignard reagents with a representative series of simple cis-2-keto-4-substituted-1,3-dioxanes have been investigated. The stereochemical outcome of these highly diastereoselective additions (dr > 90:10) is consonant with Cram's chelate model on the assumption that RMgX coordinates preferentially with the ring oxygen remote from the C(4) substituent.
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA. bailey@uconn.edu
authors.forename: W F
authors.initials: WF
authors.lastname: Bailey
authors.forename: D P
authors.initials: DP
authors.lastname: Reed
authors.forename: D R
authors.initials: DR
authors.lastname: Clark
authors.forename: G N
authors.initials: GN
authors.lastname: Kapur