𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and catalytic activity of 10-(aminomethyl)isoborneol-based catalysts: the role of the C(2)-group on the asymmetric induction

✍ Scribed by Antonio Garcı́a Martı́nez; Enrique Teso Vilar; Amelia Garcı́a Fraile; Santiago de la Moya Cerero; Beatriz Lora Maroto

Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
164 KB
Volume
14
Category
Article
ISSN
0957-4166

No coin nor oath required. For personal study only.

✦ Synopsis

Five enantiopure C(2)-substituted 10-[(dimethylamino)methyl]isoborneols has been prepared by a novel straightforward camphor-based route, and probed as d-amino-alcohol ligands for the enantioselective addition of diethylzinc to benzaldehyde. The established route constitutes a divergent model procedure for this class of d-amino-isoborneol ligands, allowing different substitutions, not only at the nitrogen atom, but also at the more interesting hydroxyl-bearing C(2)-norbornane position. This last synthetic possibility has made possible a study of the role played by the group located at the C(2)-norbornane position on the catalytic activity. New catalyst models and transition-state models for explaining such a role are also proposed and discussed.

📜 SIMILAR VOLUMES

Synthesis of a new C2-symmetric chiral c
Synthesis of a new C2-symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones
✍ Yan Zhou; Wen-Hua Wang; Wei Dou; Xiao-Liang Tang; Wei-Sheng Liu 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 English ⚖ 120 KB 👁 2 views

## Abstract A new __C__~2~‐symmetric chiral catalyst 3,5‐bis[(2__S__)‐(hydroxy‐diphenylmethyl)‐ pyrrolidin‐1‐ylmethyl]‐1,3,4‐oxadiazole was successfully synthesized by the reaction of 2,5‐dichloromethyl‐1,3,4‐oxadiazole with (__S__)‐α,α‐diphenyl‐2‐pyrrolidinemethanol, and applied to the catalytic a