Functionalised trichlorosilanes in the asymmetric allylation

QD Chemistry

Kysilka, Ondřej ; Kocovsky, Pavel

University:University of Glasgow

Department:School of Chemistry

关键词: trichlorosilane, disilane, organocatalysis, organocatalyst, asymmetric synthesis, allylation, asymmetric allylation, homoallylic alcohols, tetrahydrofurans, tetrahydropyrans, dihydropyrans, diols, building blocks, asymmetric aldol reaction, axial chirality, aminal, METHOX, QUINOX, PINDY, PINDOX, Sigamide, Kenamide, natural products, Speranskatine A, Convolutamydine A;   

Others  :  http://theses.gla.ac.uk/4377/1/2013KysilkaPhD.pdf

来源: University of Glasgow

【 摘 要 】

We present a synthetic route to the homoallylic alcohols, using the well-established asymmetric organocatalysed allylation of aldehydes. These alcohols were transformed in one step into the substituted tetrahydrofurans in the presence of achiral Lewis acids, forming three chiral centres for the price of two. A synthetic route towards chiral substituted tetrahydropyrans and unsaturated 1,5 diol-building blocks has also been developed.