343598-64-1Relevant articles and documents
Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids
Takeda, Youhei,Toyoda, Kazuya,Sameera,Tohnai, Norimitsu,Minakata, Satoshi
supporting information, p. 2796 - 2805 (2021/04/15)
We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).
Chiral-Directing-Group-Assisted Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C?H Bond to Aldimines with Subsequent Intramolecular Cyclization
Cai, Xuhong,Chen, Wenkun,Nie, Ruifang,Wang, Jun
supporting information, p. 16611 - 16615 (2021/10/19)
By using a chiral directing group, an asymmetric rhodium(III)-catalyzed C?H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved (up to 68 % yield, up to 93 % ee). A three-component variant that resembles Mannich reaction was also realized (41 % yield, 83 % ee). Product elaborations and preliminary mechanistic studies were described.
Visible-light, iodine-promoted formation of n-sulfonyl imines and n-alkylsulfonamides from aldehydes and hypervalent iodine reagents
Hopkins, Megan D,Brandeburg, Zachary C.,Hanson, Andrew J.,Lamar, Angus A
, (2018/08/04)
Alternative synthetic methodology for the direct installation of sulfonamide functionality is a highly desirable goal within the domain of drug discovery and development. The formation of synthetically valuable N-sulfonyl imines from a range of aldehydes,