Silver-Catalyzed Enantioselective Mannich Reaction of Diazoacetate Esters with N‑Boc Aldimines

The highly enantioselective Mannich reaction of diazoacetate esters with N-Boc aldimines catalyzed by silver­(I) triflate in the presence of (R)-DM-SEGPHOS is reported. The reaction is broad in scope with respect to the (hetero)­aromatic aldehyde-derived aldimine and tolerates significant variabilit...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 4; pp. 2785 - 2792
Main Authors Robertson, Gerard P, Farley, Alistair J. M, Dixon, Darren J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ASYMMETRIC-SYNTHESIS
ACID
METAL CARBENE
ISOQUINOLINE
IMINES
AZIRIDINATION
OXIDES
ISOCYANOACETATES
DIAZOESTERS
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Summary:The highly enantioselective Mannich reaction of diazoacetate esters with N-Boc aldimines catalyzed by silver­(I) triflate in the presence of (R)-DM-SEGPHOS is reported. The reaction is broad in scope with respect to the (hetero)­aromatic aldehyde-derived aldimine and tolerates significant variability of the diazoacetate ester component. Yields and enantioselectivities are good to excellent, and the reaction can be performed on a gram scale with catalyst loadings as low as 1 mol %.
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.9b03177