Diastereoselective alkylation of chiral 2-imidazolidinone glycolates: asymmetric synthesis of α-hydroxy carboxylic acids |
| |
| Institution: | 1. Department of Applied Chemistry, Chonnam National University, Gwangju 500-757, South Korea;2. Department of Chemistry and Institute of Basic Science, Chonnam National University, Gwangju 500-757, South Korea;1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky Prosp., 119991 Moscow, Russian Federation;2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, Vavilova Str., 119991 Moscow, Russian Federation;1. Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche (STEBICEF), Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy;2. Dipartimento di Medicina Molecolare, Università degli Studi di Padova, Via Gabelli 63, 35121 Padova, Italy;3. Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 10, 27100 Pavia, Italy;1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;2. Pharmacology Department, Faculty of Veterinary Medicine, Suez Canal University, Ismailia 41522, Egypt;3. Pharmacology and Toxicology Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;4. Medicinal Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;1. Institute of Chemical Materials, China Academy of Engineering Physics (CAEP), P.O. Box 919-326, Mianyang, Sichuan 621900, China;2. Department of Mechanical Engineering, City University of Hong Kong, 83 Tat Chee Avenue, Hong Kong;3. School of Physical Science and Information Technology, Liaocheng University, Liaocheng 252000, China |
| |
| Abstract: | Sodium enolates of chiral 2-imidazolidinone glycolates reacted with alkyl halides to produce α-alkylated products with high diastereoselectivities, which were readily removed by simple alkaline hydrolysis and were converted to the protected α-hydroxy carboxylic acids. The new stereogenic center was assigned the (R)-configuration by comparison with known compounds. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
