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ChemInform Abstract: A Ternary Complex Reagent for an Asymmetric Reaction of Lithium Ester Enolates with Imines.

✍ Scribed by H. FUJIEDA; M. KANAI; T. KAMBARA; A. IIDA; K. TOMIOKA

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Enolates with Imines.

-Based on a ternary complex reagent, which comprises three components, a chiral ether ligand, an achiral lithium amide and (I), the asymmetric addition of (I) to an imine (II) leads to the Ξ²-lactams such as (III) and (V) in high enantiomeric excess. The enantioselectivity and reactivity of the ternary complex depend on the size and nature of the lithium amide used. Best results are obtained under condition B). -

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A Factor Affecting Enantioselective Reaction of a Ternary Complex of Lithium Ester Enolate with Imine. -Lithiation of esters such as (I) followed by coupling of the resulting enolates with imines [cf. (II)] in the presence of chiral ether ligands is investigated systematically. Under improved react