title: Low-valent titanium-mediated stereoselective alkylation of allylic alcohols.
abstract: We have developed low-valent titanium-mediated 1,3-transpositive cross-coupling reactions of acyclic and cyclic allylic alcohols for the stereoselective introduction of ethyl, 2-silylethyl, 2-phenethyl, and alkenyl groups. Cross-coupling of an allylic alcohol with a vinylsilane or styrene derivative is particularly noteworthy, as an efficient cross-selective coupling of two alkenes has been elusive. The stereochemistry of the cross-coupling alkylation is consistent with syn addition/beta-elimination.
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
authors.forename: Ivan L
authors.initials: IL
authors.lastname: Lysenko
authors.forename: Keunho
authors.initials: K
authors.lastname: Kim
authors.forename: Hyung Goo
authors.initials: HG
authors.lastname: Lee
authors.forename: Jin Kun
authors.initials: JK
authors.lastname: Cha
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D003432:Cross-Linking Reagents / Q000737:chemistry; D004986:Ether / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003432:Cross-Linking Reagents; D020005:Propanols; D004986:Ether; C006463:allyl alcohol; D014025:Titanium