An Efficient and Convenient Method for the Asymmetric Allylation of Aldehydes with Allyltrimethylsilane Catalyzed by Diphenylboryl Triflate
- 5 June 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 16 (6) , 1121-1124
- https://doi.org/10.1246/cl.1987.1121
Abstract
In the presence of a catalytic amount of diphenylboryl triflate, aldehydes smoothly react with (S)-1-phenyl-1-trimethylsilyloxyethane and allyltrimethylsilane to afford the chiral homoallyl ethers in good yields with high stereoselectivities.Keywords
This publication has 22 references indexed in Scilit:
- Reactions of diisopropyl tartrate modified allyl- and (E)- and (Z)-crotylboronates with .beta.-alkoxy-.alpha.-methylpropionaldehydes: a reagent-based solution to the acyclic dipropionate problemThe Journal of Organic Chemistry, 1987
- .beta.-Allyldiisopinocampheylborane: a remarkable reagent for the diastereoselective allylboration of .alpha.-substituted chiral aldehydesThe Journal of Organic Chemistry, 1987
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986
- Diastereo- and enantioselective aldehyde addition reactions of 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylic esters, a useful class of tartrate ester modified allylboronatesJournal of the American Chemical Society, 1985
- Synthesis of optically active allyltin compounds and their application to enantioselective synthesis of secondary homoallyl alcoholsOrganometallics, 1985
- Highly Enantioselective Homoaldol Additions with Chiral N‐Allylureas—Application to the Synthesis of Optically Pure γ‐LactonesAngewandte Chemie International Edition in English, 1984
- Enantioselective Grignard-type addition of allyltitanium reagents having the center of chirality at titaniumOrganometallics, 1984
- Transfer of Chirality in the Addition of Chiral α‐Chloroallylboronate Esters to AldehydesAngewandte Chemie International Edition in English, 1984
- Enantioselective allylborane condensationsJournal of the American Chemical Society, 1982
- Stereoselektive Synthese von Alkoholen, VII1) Optisch aktive Homoallylalkohole durch Addition chiraler Boronsäureester an AldehydeEuropean Journal of Inorganic Chemistry, 1981