Open AccessGold(I) Catalysis Applied to the Stereoselective Synthesis of Indeno[2,1-b]thiochromene Derivatives and Seleno Analogues
Author(s) -
Cintia Virumbrales,
Mahmoud Abd El Aleem Ali Ali ElRemaily,
Samuel SuárezPantiga,
Manuel A. FernándezRodríguez,
Félix Rodríguez,
Roberto Sanz
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.2c03411
Subject(s) - chemistry , cyclopropane , stereoselectivity , intramolecular force , carbene , thio , aryl , catalysis , enantioselective synthesis , combinatorial chemistry , ring (chemistry) , stereochemistry , selenium , medicinal chemistry , organic chemistry , alkyl
A gold(I)-catalyzed cascade reaction for the stereoselective synthesis of sulfur- or selenium-containing indeno[1,2- b ]chromene derivatives from o -(alkynyl)styrenes substituted at the triple bond with a thio- or seleno-aryl group is described. The reaction involves a double cyclization process through a proposed key gold-cyclopropyl carbene intermediate that evolves by the intramolecular addition of an aromatic to the cyclopropane ring, affording polycyclic structures. The enantioselective version was studied using gold(I) complexes bearing chiral ligands.