Asymmetric Allylation with a New Chiral Allylating Agent Prepared from Tin(II) Triflate, Chiral Diamine, and Allylaluminum
- 1 October 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (10) , 3697-3704
- https://doi.org/10.1246/bcsj.60.3697
Abstract
A chiral allylating agent, readily generated from tin(II) trifluoromethanesulfonate (tin(II) triflate), chiral diamines derived from (S)-proline and allylaluminum, is efficiently employed in the asymmetric allylation of aldehydes and an epoxide. Reaction of a chiral 2-methyl-2-propenylating (methallylating) agent with aldehydes also proceeds smoothly to afford the corresponding homoallylic alcohols in good yields with high enantioselectivities. According to a similar procedure, asymmetric propargylation of aldehydes affords homopropargylic alcohols in good optical purities.Keywords
This publication has 38 references indexed in Scilit:
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986
- 3,3-Dimethylallyldiisopinocampheylborane: A novel reagent for chiral isoprenylation of aldehydes. Synthesis of (+)- and (−)-artemisia alcohol in exceptionally high enantiomeric purityTetrahedron Letters, 1984
- Asymmetric methallylboration of prochiral aldehydes with methallyldiisopinocampheylborane·synthesis of 2-methyl-1-alken-4-ols in ≥ 90% enantiomeric puritiesTetrahedron Letters, 1984
- Synthetic control leading to chiral compoundsTetrahedron, 1984
- Asymmetric carbon-carbon bond formation via .beta.-allyldiisopinocampheylborane. Simple synthesis of secondary homoallylic alcohols with excellent enantiomeric puritiesJournal of the American Chemical Society, 1983
- Enantioselective allylborane condensationsJournal of the American Chemical Society, 1982
- Stereoselektive Synthese von Alkoholen, VI1) Asymmetrische Synthesen von 4‐Penten‐2‐ol über Allylboronsäureester chiraler GlycoleEuropean Journal of Inorganic Chemistry, 1981
- Stereoselektive Synthese von Alkoholen, VII1) Optisch aktive Homoallylalkohole durch Addition chiraler Boronsäureester an AldehydeEuropean Journal of Inorganic Chemistry, 1981
- Enantioselective Synthesis of Homoallyl Alcohols via Chiral Allylboronic EstersAngewandte Chemie International Edition in English, 1978
- Macrolides. Recent Progress in Chemistry and BiochemistryAngewandte Chemie International Edition in English, 1977