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A superior chiral auxiliary in aldol condensation: camphor-based oxazolidone

✍ Scribed by Tu-Hsin Yan; Vir-Vir Chu; Ta-Chin Lin; Woei-Hung Tseng; Tun-Wen Cheng

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
208 KB
Volume
32
Category
Article
ISSN
0040-4039

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📜 SIMILAR VOLUMES

(S)-Ethyl 4,4-dimethyl pyroglutamate as
(S)-Ethyl 4,4-dimethyl pyroglutamate as a new ‘quat’ chiral auxiliary in aldol condensations
✍ Jesús Ezquerra; Almudena Rubio; Justina Martín; JoséLuis García Navío 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 152 KB

Enolates I, derived from the N-propionyl derivative of the 'quat' chiral auxiliary (S)-ethyl 4,4-dimethyl pyroglutamate 4 undergo highly stereoselective aldol reactions, which upon hydrolysis and removal of the chiral auxiliary yields the (2R,3R)-3-hydroxy-2-methylpropionic acid 9 in homochiral form

ChemInform Abstract: (S)-Ethyl 4,4-Dimet
ChemInform Abstract: (S)-Ethyl 4,4-Dimethyl Pyroglutamate as a New “Quat” Chiral Auxiliary in Aldol Condensations.
✍ J. EZQUERRA; A. RUBIO; J. MARTIN; J. L. GARCIA NAVIO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 1 views

The title pyroglutamate (II) is found to be an excellent auxiliary in stereoselective aldol reactions. Remarkably, the stereogenic center of (II) is not altered during all the transformations and (II) can be regenerated after the process in 70% yield. -(EZQUERRA, J.;