Enantioselective Copper-Catalyzed Oxy-Alkynylation of Diazo Compounds

Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds using ethynylbenziodoxol-(on)­e reagents and a s...

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Published inJournal of the American Chemical Society Vol. 139; no. 25; pp. 8420 - 8423
Main Authors Hari, Durga Prasad, Waser, Jerome
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MULTICOMPONENT REACTIONS
CARBENE
COOPERATIVE CATALYSIS
EFFICIENT APPROACH
COUPLING REACTIONS
3-COMPONENT REACTION
AMMONIUM YLIDES
OXONIUM YLIDES
H INSERTION REACTIONS
MICHAEL ADDITION
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Summary:Enantioselective catalytic methods allowing the addition of both a nucleophile and an electrophile onto diazo compounds give a fast access into important building blocks. Herein, we report the highly enantioselective oxyalkynylation of diazo compounds using ethynylbenziodoxol-(on)­e reagents and a simple copper bisoxazoline catalyst. The obtained α-benzoyloxy propargylic esters are useful building blocks, which are difficult to synthesize in enantiopure form using other methods. The obtained products could be efficiently transformed into vicinal diols and α-hydroxy propargylic esters without loss in enantiopurity.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b04756