Enantioselective Alkylation of Aldehydes with Chiral Organomagnesium Amides (COMAs)
- 19 September 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (21) , 3553-3556
- https://doi.org/10.1021/ol0258132
Abstract
Dialkylmagnesiums react with chiral secondary amines to form chiral organomagnesium amides (COMAs). These reagents alkylate aldehydes to form secondary alcohols with enantioselectivities up to 91:9 er.Keywords
This publication has 6 references indexed in Scilit:
- Reactions between primary amines and magnesium or zinc dialkyls: intermediates in metal imide formationInorganica Chimica Acta, 1996
- Enantioselective conjugate addition to cyclic enones with scalemic lithium organo(amido)cuprates, Part IV. Relationship between ligand structure and enantioselectivityTetrahedron, 1993
- Reactions of chelating alkali metal amides with the Grignard reagent nBuMgCl: crystal structures and solution 1H NMR spectroscopic studies of the expected mono(amido)-product [PhCH2(Me2NCH2CH2)NMgnBu]2 and the unexpected bis(amido)-product {[Ph(2-Pyr)N]2M9 · (THF)2}Journal of Organometallic Chemistry, 1992
- Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohols. Mechanism and nonlinear effectJournal of the American Chemical Society, 1989
- Enantioface-differentiating (asymmetric) addition of alkyllithium and dialkylmagnesium to aldehydes by using (2S,2'S)-2-hydroxymethyl-1-[(1-alkylpyrrolidin-2-yl)methyl]pyrrolidines as chiral ligandsJournal of the American Chemical Society, 1979
- Stereochemistry of polynuclear compounds of the main group elements. VIII. The crystal structure of bis[2-dimethylaminoethyl(methyl)amino]di(methylmagnesium)Inorganic Chemistry, 1969