Intramolecular Consecutive Dehydro‐Diels–Alder Reaction for the Catalytic and Enantioselective Construction of Axial Chirality

Abstract

Consecutive thermal and metal-catalyzed dehydro-Diels-Alder (DDA) reactions of sulfur-tethered tetraynes, possessing a1 ,3-diyne moiety,proceeded efficiently,a nd axial chirality was achieved for the resulting dibenzothiophenyl moieties.C hiral-rhodium catalysis realized ah ighly enantioselective synthesis,a nd transformations into bis(benzocarbazole) derivatives were also achieved.Scheme 2. General scheme and synthetic use of the DDA reactions.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

Atroposelective desymmetrization of 2-arylresorcinols via Tsuji-Trost allylation

“…T he development of catalytic and enantioselective syntheses of axially chiral biaryls has been extensively explored [1][2][3][4][5][6][7] because it provides a highly efficient and selective route to access natural products 8,9 , biologically active compounds [10][11][12] , and chiral catalysts [13][14][15] . Strategies to control a stereogenic axis are generally classified into several categories [16][17][18][19][20][21][22][23] , such as direct cross-coupling, dynamic kinetic resolution, ring formation, and desymmetrization (Fig.…”

Organocatalytic Atroposelective Reactions of Alkynes

“…In recent decades, the catalytic asymmetric transformation of alkynes has emerged as an important protocol to access axially chiral compounds. 5 A variety of transition-metal-catalyzed atroposelective reactions of alkynes have been developed, such as (2+2+2) cycloaddition, 6 intramolecular cyclization, 7 alkyne insertion, 8 Diels–Alder reaction, 9 and others. 10 Alternatively, the related organocatalytic transformations of alkynes have received increasing interest recently.…”