Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents.
Org Lett
; 23(16): 6530-6535, 2021 08 20.
Article
em En
| MEDLINE
| ID: mdl-34374544
ABSTRACT
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Triazóis
/
Ciclobutanos
/
Ciclopropanos
/
Alcenos
/
Alcinos
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article