Low-valent titanium-mediated stereoselective alkylation of allylic alcohols.
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.
Lysenko
Ivan L
IL
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
Kim
Keunho
K
Lee
Hyung Goo
HG
Cha
Jin Kun
JK
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*
D000475:Alkenes; D003432:Cross-Linking Reagents; D020005:Propanols; D004986:Ether; C006463:allyl alcohol; D014025:Titanium