Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents

Autor:	Sajan C. Patel, Noah Z. Burns, Myles W. Smith, Jaron A. M. Mercer, Kensuke Suzuki
Rok vydání:	2021
Předmět:	Sulfonyl chemistry.chemical_classification Cyclobutanes Organic Chemistry Enantioselective synthesis Alkyne Hydrazide Biochemistry Combinatorial chemistry Cycloaddition chemistry.chemical_compound chemistry Tosyl Diazo Physical and Theoretical Chemistry
Zdroj:	Organic Letters. 23:6530-6535
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c02331
Popis:	Cyclobutenes are highly useful synthetic intermediates as well as important motifs in bioactive small molecules. Herein, we report a regio-, chemo-, and enantioselective synthesis of cyclobutenes from olefins using N-sulfonyl-1,2,3-triazoles as vicinal dicarbene equivalents or alkyne [2 + 2] cycloaddition surrogates. Terminal and cis-olefins can be transformed into enantioenriched cyclopropanes via rhodium catalysis. Then, in one pot, treatment of these intermediates with tosyl hydrazide and base effects diazo formation followed by rhodium-catalyzed ring expansion to yield enantioenriched cyclobutenes. These cyclobutenes can be transformed into highly substituted, enantioenriched cyclobutanes, including structures relevant to natural product scaffolds.
Databáze:	OpenAIRE
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