Regulation of Diastereofacial Selection in the Allylation Reaction of N-Acyliminium Ion Utilizing Lewis Acids
- 1 February 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 22 (2) , 221-224
- https://doi.org/10.1246/cl.1993.221
Abstract
Diastereofacial selectivity in the α-allylation reaction of chiral cyclic α-acyloxy amide, derived from succinic anhydride and (R)-2-methoxy-1-phenylethylamine could be regulated using appropriately selected Lewis acids; i.e., the reaction using Lewis acids such as TiCl4 gave (R,S)-α-allylated amides, while allylation promoted by SnCl4 afforded (R,R)-isomers stereoselectively. The similar result was obtained in the reaction of chiral amide prepared from phthalic anhydride.Keywords
This publication has 12 references indexed in Scilit:
- Diastereoface-discrimination reaction of lithium or titanium ester enolates with a chiral imine leading to stereodivergent synthesis of β-lactamsTetrahedron, 1992
- Asymmetric synthesis of .gamma.,.gamma.-dialkyl-.gamma.-aminobutyric acid analogs and 2,2-disubstituted pyrrolidines. Control of stereochemistry in aminal ring opening by varying the extent of allylic 1,3 strainJournal of the American Chemical Society, 1991
- Enantiomerically pure polyhydroxylated acyliminium ions. Synthesis of the glycosidase inhibitors (-)-swainsonine and (+)-castanospermineJournal of the American Chemical Society, 1990
- Enantioselective total syntheses of indolizidine alkaloids 167B and 209DThe Journal of Organic Chemistry, 1990
- Diastereoselectivity of organometallic additions to nitrones bearing stereogenic N-substituentsThe Journal of Organic Chemistry, 1990
- Stereoselective nucleophilic additions to the carbon-nitrogen double bond. 3. Chiral acyliminium ionsThe Journal of Organic Chemistry, 1990
- Organocerium additions to SAMP-hydrazones: general synthesis of chiral aminesJournal of the American Chemical Society, 1987
- Enantioselective Synthesis of α‐Substituted Primary Amines by Nucleophilic Addition to Aldehyde‐SAMP HydrazonesAngewandte Chemie International Edition in English, 1986
- Intramolecular reactions of N-acyliminium intermediatesTetrahedron, 1985
- Very high 1,2-asymmetric induction in the reaction of allyl-9-BBN with certain imines. Evidence for a stereoelectronic effect to enhance the Cram selectivityJournal of the American Chemical Society, 1984