Theoretical Mechanistic Investigation of the Dynamic Kinetic Resolution of N-Protected Amino Acid Esters using Phase-Transfer Catalysts

被引：3

作者：

Yamamoto, Eiji ^{[1
]}

Kobayashi, Kaoru ^{[1
]}

Wakafuji, Kodai ^{[1
]}

Kamachi, Takashi ^{[2
]}

Tokunaga, Makoto ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Chem, Fukuoka 8190395, Japan

[2] Fukuoka Inst Technol, Dept Life Environm & Appl Chem, Fukuoka 8110295, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 12期

关键词：

GAUSSIAN-BASIS SETS; ENANTIOSELECTIVE HYDROLYSIS; ATOMS LI; PROTONATION; HISTIDINE; SEARCH; FIELD;

D O I：

10.1021/acs.joc.2c02352

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 p-stacking interactions are the common important features of the proposed TS structures that determine the stereoselectivity.

引用

页码：7748 / 7754

页数：7

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