Abstract
One-pot asymmetric allylation of aldehydes and glyoxylates with `C-centered' chiral pentacoordinate allylsilicates generated from a chiral diol-modified allyltrichlorosilane 8 in the presence of Lewis bases, gave optically active homoallylic alcohols 4 with relatively high enantioselectivity (up to 81% ee). The reactions proceed via a six-membered cyclic transition state. In contrast, the allylation reactions of glyoxylate with allylalkoxysilanes promoted by TiCl 4 proceed through an acyclic transition state. The chiral auxiliaries residing at different positions on the molecules exhibited different abilities for asymmetric induction, depending on the reaction pathway and the stereochemistry of the transition state.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
