Rational design of novel axially chiral NADH models based on configurational control of atropisomeric lactams
✍ Scribed by Jean-Luc Vasse; Georges Dupas; Jack Duflos; Guy Quéguiner; Jean Bourguignon; Vincent Levacher
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 98 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The preparation of a new class of axially chiral NADH models based on configurational control of atropisomeric lactams is described. The configurational control of this chiral axis is achieved via the presence of a second chirality element installed on the lactam moiety of the reagent 2. Reduction of methyl benzoylformate led to methyl mandelate in 89% yield and 92% e.e. This result suggests that the chiral axis about C3 C O bond is the main configurational element responsible for the high enantioselectivity observed with this biomimetic model.