ChemInform Abstract: Stereoselective Syntheses of Chiral Heterocycles and Alkaloids Using Carbohydrate Auxiliaries

Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-induced Asymmetric Addition of Organometallic Compounds to Imines

Arylalkylamines are of interest as building blocks for the synthesis of biologically active compounds and as chiral ligands or chiral auxiliaries in stereoselective syntheses [1]. Their stereoselective synthesis has been achieved by enantioselective reduction of ketimines using chiral reagents [2], as for example Corey’s oxaborolidines [3], or proline-derived triacyloxyborohydrides [4]. Particularly efficient asymmetric syntheses of chiral arylalkylamines have been accomplished by Noyori et al. [5] through enantioselective catalysis of hydrogen transfer reactions using a chiral 1,2-diphenyl-ethylenediamine ruthenium catalyst. Enantioselective transferhydrogenationshave also been achieved us…

ChemInform Abstract: Glycosylation-induced Asymmetric Synthesis: -Amino Acid Esters via Mannich Reactions.

ChemInform Abstract: Glycosylation-Induced Asymmetric Synthesis of 1-Substituted Tetrahydroisoquinolines.

ChemInform Abstract: Stereoselective Synthesis of α-Arylalkylamines by Glycosylation-Induced Asymmetric Addition of Organometallic Compounds to Imines.

Arylalkylamines are of interest as building blocks for the synthesis of biologically active compounds and as chiral ligands or chiral auxiliaries in stereoselective syntheses [1]. Their stereoselective synthesis has been achieved by enantioselective reduction of ketimines using chiral reagents [2], as for example Corey’s oxaborolidines [3], or proline-derived triacyloxyborohydrides [4]. Particularly efficient asymmetric syntheses of chiral arylalkylamines have been accomplished by Noyori et al. [5] through enantioselective catalysis of hydrogen transfer reactions using a chiral 1,2-diphenyl-ethylenediamine ruthenium catalyst. Enantioselective transferhydrogenationshave also been achieved us…

Glycosylation-induced asymmetric synthesis: β-amino acid esters via Mannich reactions

Abstract Activation of Schiff bases by N-glycosylation induces asymmetric Mannich reactions with O-silyl ketene acetals to give β-amino acid esters in good yields.