title: Diastereoselectivity control of the radical carboazidation of substituted methylenecyclohexanes.
abstract: A systematic study of the diastereoselectivity of the radical carboazidation of methylenecyclohexane derivatives is presented. Several substitution patterns leading to a high level of stereocontrol have been identified. Axial attack is the preferred reaction pathway for cyclohexyl radicals, and excellent stereoselectivities can be obtained by introducing an axial substitutent at position 2. In this case, a second equatorial substituent at position 2 may be tolerated without a large detrimental effect on the diastereoselectivity. Finally, a high level of equatorial attack is observed with a very bulky substituent at position 2.
authors.affiliation: Departement für Chemie and Biochemie, Universität Bern Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Sylvaine
authors.initials: S
authors.lastname: Cren
authors.forename: Pascal
authors.initials: P
authors.lastname: Schär
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
authors.forename: Kurt
authors.initials: K
authors.lastname: Schenk