Theoretical Mechanistic Investigation of the Dynamic Kinetic Resolution of N-Protected Amino Acid Esters using Phase-Transfer Catalysts
-
- Eiji Yamamoto
- Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0395, Japan
-
- Kaoru Kobayashi
- Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0395, Japan
-
- Kodai Wakafuji
- Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0395, Japan
-
- Takashi Kamachi
- Department of Life, Environment and Applied Chemistry, Fukuoka Institute of Technology, 3-30-1 Wajiro-higashi, Higashi-ku, Fukuoka 811-0295, Japan
-
- Makoto Tokunaga
- Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0395, Japan
この論文をさがす
説明
A detailed theoretical mechanistic investigation on the dynamic kinetic resolution of N-protected amino acid esters using phase-transfer catalysts is described. Semiautomatic exhaustive conformation search of transition state (TS)-like structures were carried out using the ConFinder program and the pseudo-TS conformational search (PTSCS) method. This conformational search method successfully provided reasonable TS structures for determining the stereoselectivity in the asymmetric base hydrolysis of hexafluoroisopropyl (HFIP) esters as well as the racemization mechanism. Furthermore, the independent gradient model (IGM) analysis of the TS structures suggested that the H-bonding interactions with the oxyanion hole and π-stacking interactions are the common important features of the proposed TS structures that determine the stereoselectivity.
収録刊行物
-
- The Journal of Organic Chemistry
-
The Journal of Organic Chemistry 88 (12), 7748-7754, 2023-02-06
American Chemical Society (ACS)