Asymmetric Synthesis of Glutamic Acid Derivatives by Silver-Catalyzed Conjugate Addition–Elimination Reactions

The enantioselective construction of a family of chiral glycine-derived aldimino esters is described. The asymmetric tandem conjugate addition–elimination procedure is characterized by its exceptional mild reaction conditions and features with an exquisite enantioselectivity profile using commercial...

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Published inOrganic letters Vol. 19; no. 18; pp. 4896 - 4899
Main Authors Yuan, Yang, Yu, Bo, Bai, Xing-Feng, Xu, Zheng, Zheng, Zhan-Jiang, Cui, Yu-Ming, Cao, Jian, Xu, Li-Wen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.09.2017
Amer Chemical Soc
Subjects
catalysts
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
enantioselectivity
esters
glutamic acid
Physical Sciences
schiff bases
Science & Technology
MANNICH REACTION
1,3-DIPOLAR CYCLOADDITIONS
ENANTIOSELECTIVE SYNTHESIS
ACTIVATED ALLYLIC ACETATES
ALKYLATION
BAYLIS-HILLMAN REACTION
ALPHA-AMINO-ACIDS
GLYCINE DERIVATIVES
C-H FUNCTIONALIZATION
MICHAEL ADDITION
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.7b02378

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Summary:The enantioselective construction of a family of chiral glycine-derived aldimino esters is described. The asymmetric tandem conjugate addition–elimination procedure is characterized by its exceptional mild reaction conditions and features with an exquisite enantioselectivity profile using commercially available silver/DTBM-SegPhos catalyst, allowing for the facile preparation of a variety of substituted and chiral glutamic acid derivatives (up to 99% ee) bearing Schiff base in a straightforward manner.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b02378