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A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a… Click to show full abstract
A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an α-imino carbene into the O–H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (–)-α-conhydrine is also described.
Keywords:
triazoles alkenols;
reaction sulfonyl;
rhodium catalyzed;
sulfonyl triazoles;
reaction;
catalyzed reaction
Journal Title: Helvetica Chimica Acta
Year Published: 2017
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Journal Title: Helvetica Chimica Acta
Year Published: 2017
Link to full text (if available)
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recommendations!