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β‐Diazocarbonyl Compounds: Synthesis and their Rh(II)‐Catalyzed 1,3 C−H Insertions
Author(s) -
Jiang Liyin,
Wang Zhaofeng,
Armstrong Melanie,
Suero Marcos G.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202015077
Subject(s) - hypervalent molecule , electrophile , diazo , enol , chemistry , intramolecular force , carbene , ketone , silylation , catalysis , reagent , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry
Herein, we describe the first electrophilic diazomethylation of ketone silyl enol ethers with diazomethyl‐substituted hypervalent iodine reagents that gives access to unusual β‐diazocarbonyl compounds. The potential of this unexplored class of diazo compounds for the development of new reactions was demonstrated by the discovery of a rare Rh‐catalyzed intramolecular 1,3 C−H carbene insertion that led to complex cyclopropanes with excellent stereocontrol.