✦ LIBER ✦
Increasing Enantioselectivities and Reactivities by Stereochemical Tuning: Fenchone-Based Catalysts in Dialkylzinc Additions to Benzaldehyde
✍ Scribed by Bernd Goldfuss; Melanie Steigelmann; Frank Rominger
- Book ID
- 102657916
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 505 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
Trimethylsilyl substitutions of the fenchyl alcohols [(1R,2R,4S)-exo-(2-Ar)-1,3,3-trimethylbicyclo[2.2.1]heptan-2ol, Ar = 2-methoxyphenyl (1) and Ar = 2-(dimethylaminomethyl)phenyl (2)] yield the chiral ligands 3 [Ar = 2-methoxy-3-(trimethylsilyl)phenyl] and 4 [Ar = 2-(dimethylaminomethyl)-3-(trimethylsilyl)phenyl]. Increased reactivities and enantioselectivities in diethylzinc additions to benzaldehyde are obtained from 3 (63% ee R) and 4 (93% ee S), relative to 1