NHC Organocatalysis in D2O for the Highly Diastereoselective Synthesis of Deuterated Spiropyran Analogues

被引：6

作者：

Suresh, Pavithira ^{[1
]}

Thamotharan, Subbiah ^{[2
]}

Selva Ganesan, Subramaniapillai ^{[1
]}

机构：

[1] SASTRA Deemed Univ, Dept Chem, Sch Chem & Biotechnol, Thanjavur 613401, Tamil Nadu, India

[2] SASTRA Deemed Univ, Sch Chem & Biotechnol, Biomol Crystallog Lab, Dept Bioinformat, Thanjavur 613401, Tamil Nadu, India

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 09期

关键词：

Deuteration; Diastereoselective; Spirocycle; Spiropyran; Water; CATALYZED MICHAEL ADDITION; ALPHA; BETA-UNSATURATED ALDEHYDES; DEUTERIUM; SCAFFOLDS;

D O I：

10.1002/slct.202004150

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Metal-free N-heterocyclic carbene (NHC) organocatalysis in D2O medium was elegantly utilised for the synthesis of highly diastereoselective deuterated spiropyran derivatives. Selective deuteration was exclusively achieved on the C5 carbon atom of the pyran ring. Quantum chemical calculations were performed to prove the preferential formation of a single diastereomer from the possible four diastereomers. The scope of NHC organocatalysis in D2O was also extended for the synthesis of deuterated spirooxindole derivative.

引用

页码：2036 / 2040

页数：5

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