Construction of α,β-Diamino Diacid Derivatives with Adjacent Acyclic Tetrasubstituted Stereocenters

A convenient strategy for the diastereoselective synthesis of α,β-diamino diacid derivatives bearing congested vicinal acyclic tetrasubstituted stereocenters via catalytic Mannich-type reactions of azlactones and 2-aminoacrylates was established. A diverse set of α,β-diamino diacid derivatives were...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 13; pp. 8709 - 8718
Main Authors Zhou, Feng, Hu, Qi-Long, Hou, Ke-Qiang, Chan, Albert S. C., Xiong, Xiao-Feng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AZLACTONES
BIOLOGICAL SIGNIFICANCE
OXAZOLONES
ACIDS
MANNICH REACTIONS
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Summary:A convenient strategy for the diastereoselective synthesis of α,β-diamino diacid derivatives bearing congested vicinal acyclic tetrasubstituted stereocenters via catalytic Mannich-type reactions of azlactones and 2-aminoacrylates was established. A diverse set of α,β-diamino diacid derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivity (up to 98:2 er) was achieved by employing the catalyst (DHQD)2PHAL in the subsequent asymmetric study.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00950