Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2' manifolds.
High chemoselectivity can be achieved in the addition of lithium dithiane anions to vinyl epoxides exploiting the steric nature of the dithiane substituent. Unencumbered dithiane anions afford SN2 adducts, whereas sterically encumbered anions lead primarily to SN2' adducts. Furthermore, the SN2' addition occurs syn to the vinyl epoxide.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia Pennsylvania 19104, USA. smithab@sas.upenn.edu
Pitram
Suresh M
SM
Gaunt
Matthew J
MJ
Kozmin
Sergey A
SA
D000438:Alcohols / Q000138:chemical synthesis; D004852:Epoxy Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D011807:Quinolizines; D013457:Sulfur Compounds; D014753:Vinyl Compounds; C438055:dithiane; D008094:Lithium