Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides

被引：13

作者：

Sarkale, Abhijeet M. ^{[1
]}

Maurya, Vidyasagar ^{[1
]}

Giri, Sachin ^{[1
]}

Appayee, Chandrakumar ^{[1
]}

机构：

[1] Indian Inst Technol Gandhinagar, Discipline Chem, Gandhinagar 382355, Gujarat, India

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 11期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; (+)-NEPHROSTERANIC ACID; GAMMA-BUTYROLACTONES; NATURAL-PRODUCTS; 1ST SYNTHESIS; METHYLENOLACTOCIN; KETONES; LACTONE;

D O I：

10.1021/acs.orglett.9b01445

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps with good yields and high stereoselectivities. This stereodivergent synthetic methodology is applied for the synthesis of seven bioactive paraconic acid natural products.

引用

页码：4266 / 4270

页数：5

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