Copper- and Silver-Catalyzed Diastereo- and Enantioselective Conjugate Addition Reaction of 1‑Pyrroline Esters to Nitroalkenes: Diastereoselectivity Switch by Chiral Metal Complexes

syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX catalyst in the presence of pyridine. In contrast, AgOAc/tBu-ThioClickFerrophos catalyzed the anti diastereoselective conjugate addition with a...

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Published inJournal of organic chemistry Vol. 80; no. 21; pp. 10883 - 10891
Main Authors Koizumi, Akihiro, Kimura, Midori, Arai, Yuri, Tokoro, Yuichiro, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.11.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION
DESIGN
PYRROLIDINES
LIGANDS
GLYCINE IMINO ESTER
CONSTRUCTION
AZOMETHINE YLIDES
BASIS-SETS
DERIVATIVES
MICHAEL ADDITION
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Summary:syn-Diastereoselective conjugate addition of 1-pyrroline esters to nitroalkenes in good yields with an excellent enantioselectivity by using CuOAc/Me-FcPHOX catalyst in the presence of pyridine. In contrast, AgOAc/tBu-ThioClickFerrophos catalyzed the anti diastereoselective conjugate addition with a high enantioselectivity without additional base. Thus, the preparation of chiral 1-pyrroline derivatives bearing diverse stereochemistry could be achieved. The diastereoselective reduction of the imine group in the conjugate adduct could afford the 2,5-cis-proline ester derivative.
Bibliography:KAKEN
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.5b02024