148730-42-1Relevant articles and documents
Enantioselective Cyclobutenylation of Olefins Using N-Sulfonyl-1,2,3-Triazoles as Vicinal Dicarbene Equivalents
Burns, Noah Z.,Mercer, Jaron A. M.,Patel, Sajan C.,Smith, Myles W.,Suzuki, Kensuke
, p. 6530 - 6535 (2021/09/02)
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.
The nickel and palladium catalyzed stereoselective cross coupling of cyclopropyl nucleophiles with aryl halides
De Lang,Brandsma
, p. 225 - 232 (2007/10/03)
The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with good yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)4. Other Ni- and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.
THE MATRIX EFFECT ON STEREOSELECTIVITY OF OLEFIN CYCLOPROPANATION BY ARYLCARBENE
Tomioka, Hideo,Ozaki, Yasuji,Koyabu, Yasuhiro,Izawa, Yasuji
, p. 1917 - 1920 (2007/10/02)
Temperature studies of addition of phenylcarbene to styrene showed that stereoselectivity changed rather dramatically as the reaction phase changed.
