Ligand-Controlled Stereodivergent, Enantioselective Conjugate Addition of 2‑Oxazoline- and 2‑Thiazoline-4-carboxylate to Nitroalkene Catalyzed by Chiral Copper Complexes

The copper-catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline-4-carboxylate to a nitroalkene proceeded to give either the syn or anti adduct selectively in high enantiomeric excess when an appropriate chiral ligand was used. Subsequent reduction of the nitro group followed by h...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 17; pp. 7939 - 7944
Main Authors Matsuda, Yukiko, Koizumi, Akihiro, Haraguchi, Ryosuke, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ALKYLATION
1,3-DIPOLAR CYCLOADDITION
AZOMETHINE YLIDES
ALPHA-AMINO-ACIDS
GAMMA-ADDITIONS
TERT-BUTYL ESTER
DERIVATIVES
MICHAEL ADDITION
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Summary:The copper-catalyzed asymmetric conjugate addition of 2-oxazoline- and 2-thiazoline-4-carboxylate to a nitroalkene proceeded to give either the syn or anti adduct selectively in high enantiomeric excess when an appropriate chiral ligand was used. Subsequent reduction of the nitro group followed by hydrolysis of the oxazoline ring yielded an optically active γ-lactam of protected α-quaternary serine derivative.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01722