Origin of Enantioselectivity in Chiral Phosphoric-Acid-Catalyzed Azlactone Dynamic Kinetic Resolution

被引：5

作者：

De Castro, Pedro P. ^{[3
]}

Batista, Gabriel M. F. ^{[1
,2
]}

Amarante, Giovanni W. ^{[3
]}

Dos Santos, Helio F. ^{[3
]}

机构：

[1] Aarhus Univ, Carbon Dioxide Activat Ctr CADIAC, Interdisciplinary Nanosci Ctr iNANO, DK-8000 Aarhus, Denmark

[2] Aarhus Univ, Dept Chem, DK-8000 Aarhus, Denmark

[3] Univ Fed Juiz de Fora, Chem Dept, BR-36036900 Juiz De Fora, MG, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 18期

关键词：

ASYMMETRIC-SYNTHESIS; HYDROAMINATION; ALLENES;

D O I：

10.1021/acs.joc.1c01882

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Theoretical calculations, associated with control experiments, were carried out to gain insights into the mechanism and origin of enantioselectivity in the phosphoric-acid-catalyzed dynamic kinetic resolution of azlactones. The results revealed a Munchnone intermediate as the key species involved in the isomerization of azlactone rings. The developed model was successfully employed in the comprehension and prediction of enantioselectivity under diverse of reaction conditions, including alcoholysis and aminolysis protocols.

引用

页码：13169 / 13174

页数：6

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