35901-76-9Relevant articles and documents
Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
Bonilla, Pablo,Rey, Yannick P.,Holden, Catherine M.,Melchiorre, Paolo
supporting information, p. 12819 - 12823 (2018/09/20)
Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical-based bond-forming events, the method converts unactivated olefins and α,β-unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three-component radical cascade further demonstrates the complexity-generating power of this photochemical strategy.
Stereocontrolled total syntheses of optically active furofuran lignans
Inai, Makoto,Ishikawa, Ryo,Yoshida, Naoto,Shirakawa, Nana,Akao, Yusuke,Kawabe, Yusuke,Asakawa, Tomohiro,Egi, Masahiro,Hamashima, Yoshitaka,Kan, Toshiyuki
, p. 3513 - 3521 (2015/11/17)
Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.
Total syntheses of (+)-sesamin and (+)-sesaminol
Ishikawa, Ryo,Yoshida, Naoto,Akao, Yusuke,Kawabe, Yusuke,Inai, Makoto,Asakawa, Tomohiro,Hamashima, Yoshitaka,Kan, Toshiyuki
supporting information, p. 1572 - 1574 (2015/02/19)
Total syntheses of (+)-sesamin (1a ) and (+)-sesaminol (1b), which are major components of sesame lignans derived from Sesamum indicum, were accomplished in a highly stereo-controlled manner. Key steps include an L-proline-catalyzed cross-a ldol reaction, which was accelerated with the aid of bifunctional urea 7, and the construction of a furofuran lignan skeleton through a quinomethide intermediate.
