105643-15-0Relevant articles and documents
Enantioselective synthesis of 3-substituted dihydrobenzofurans through iridium-catalyzed intramolecular hydroarylation
Nishimura, Takahiro,Sakamoto, Kana
supporting information, p. 684 - 690 (2021/02/06)
Intramolecular hydroarylationviaC-H activation is one of the most powerful methods to synthesize carbo- and heterocyclic compounds, whereas we still have room for developing a highly enantioselective variant of the reaction. Here we describe Ir-catalyzed enantioselective intramolecular hydroarylation ofm-allyloxyphenyl ketones. The enantioselective cyclization was efficiently catalyzed by a cationic iridium complex coordinated with a conventional chiral bisphosphine ligand to give benzofurans in high yields with high enantioselectivity. A carbonyl group of ketones functioned as an effective directing group for the C-H activation. In terms of synthetic utility, we also achieved one-pot synthesis of chiral 3-substituted dihydrobenzofurans from readily available allylic carbonates andm-hydroxyacetophenonesviasequential Pd-catalyzed allylic substitution and Ir-catalyzed intramolecular hydroarylation.
Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information, p. 11940 - 11944 (2017/09/20)
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.
Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis
Huo, Xiaohong,He, Rui,Fu, Jingke,Zhang, Jiacheng,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 9819 - 9822 (2017/08/02)
We report a stereoselective and site-specific allylic alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.
Sterically controlled alkylation of arenes through iridium-catalyzed C-H borylation
Robbins, Daniel W.,Hartwig, John F.
supporting information, p. 933 - 937 (2013/02/25)
Complementary chemistry: A one-pot method for the site-selective alkylation of arenes controlled by steric effects is reported. The process occurs through Ir-catalyzed C-H borylation, followed by Pd- or Ni-catalyzed coupling with alkyl electrophiles. This selectivity complements that of the typical Friedel-Crafts alkylation; meta-selective alkylation of a broad range of arenes with various electronic properties and functional groups occurs in good yield with high site selectivity. Copyright