Enantioselective Access to Chiral 2,5-Diketopiperazines via Stereogenic-at-Cobalt(III)-Catalyzed Ugi-4CRs/Cyclization Sequences

An asymmetric synthesis of chiral 2,5-diketopiperazines by the Ugi-4CR/cyclization is exhibited. The employment of catalytic anionic chiral Co­(III) complexes delivered α-propiolyl aminoamides in high yields with excellent enantioselectivities (31 examples, up to 95% ee). The following treatment of...

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Published inJournal of organic chemistry Vol. 88; no. 22; pp. 16024 - 16037
Main Authors Fang, Wei, Sun, Bing-Bing, Qin, Shi-Cheng, Fang, Li-Ping, Yu, Xin-Ran, Jiang, Hua-Jie, Yu, Jie
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.11.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
MULTICOMPONENT REACTIONS
DIKETOPIPERAZINES
COMPLEXES
CONSTRUCTION
ALPHA-ADDITION
UGI REACTION
PIPERAZINES
TRANSFORMATIONS
CYCLIZATION
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Summary:An asymmetric synthesis of chiral 2,5-diketopiperazines by the Ugi-4CR/cyclization is exhibited. The employment of catalytic anionic chiral Co­(III) complexes delivered α-propiolyl aminoamides in high yields with excellent enantioselectivities (31 examples, up to 95% ee). The following treatment of Ugi-adducts with PPh3 leads to chiral 2,5-DKPs without significant loss of enantioselectivities (26 examples, up to 91% ee).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02013