A direct aerobic oxidative dehydrogenative coupling reaction of glycine derivatives with electron-rich arenes has been accomplished via the synergistic combination of organic-dye mediated photoredox catalysis and Lewis acid catalysis. This process exhibits good tolerance of functional groups and provides rapid synthesis of arylglycine derivatives at room temperature under an air atmosphere. Moreover, this protocol could be performed on a 10 mmol scale, without obvious reduction of the yield.
A previously proposed triene of the lindenane skeleton was synthesized, characterized, and identified as the common intermediate for the non-enzymatic synthesis of natural lindenane oligomers through linear, [4+2]-type and [6+6]-type homo-and hetero-dimerization under simulated physiological conditions. As a result, the following six natural products were successfully synthesized through thermal head-to-head, head-totail, and head-to-back binding modes: shizukaols A and J, cycloshizukaol A, chlorahupetone F, chlotrichene B, and trishizukaol A.
A previously proposed triene of the lindenane skeleton was synthesized, characterized, and identified as the common intermediate for the non‐enzymatic synthesis of natural lindenane oligomers through linear, [4+2]‐type and [6+6]‐type homo‐ and hetero‐ dimerization under simulated physiological conditions. As a result, the following six natural products were successfully synthesized through thermal head‐to‐head, head‐to‐tail, and head‐to‐back binding modes: shizukaols A and J, cycloshizukaol A, chlorahupetone F, chlotrichene B, and trishizukaol A.
A photo-triggered cascade cyclization of silyl enolate to prepare
angularly fused tricyclic scaffold is developed. The reaction
demonstrates good substrate scope and stereo-selectivity. The excellent
stereo- and regio-selectivity for this cascade reaction is elucidated
via conformational analysis and DFT calculation, respectively.
Comprehensive SummaryPhoto‐induced electron transfer (PET) of silyl enol ethers has been employed to synthesize several fused ring systems. However, the method has limited applicability due to its narrow substrate scope, low product yields, unsatisfactory stereo‐ and regioselectivity. Herein, we report a PET‐triggered cascade reaction of silyl enolates that leads to the formation of angularly fused tricyclic scaffolds. The reaction exhibits broad substrate scope and excellent stereoselectivity. The regio‐ and stereoselectivity of this cascade reaction is elucidated via DFT calculation and conformational analysis.
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