Enantioselective Heck/Tsuji−Trost Reaction of Flexible Vinylic Halides with 1,3-Dienes

Research Square (Research Square), Год журнала: 2024, Номер unknown

Опубликована: Авг. 16, 2024

The enantioselective domino Heck/cross-coupling has emerged as a powerful tool in modern chemical synthesis for decades. Despite significant progress relative rigid skeleton substrates, the implementation of asymmetric cascades highly flexible haloalkene substrates remains challenging and long-standing goal. Here we report an efficient tandem Heck/Tsuji−Trost reaction vinylic halides with 1,3-dienes enabled by palladium catalysis. A variety functional cyclic isoprenoids, which are key structural motifs numerous natural products family, were delivered good yields excellent regio-, diastereo- enantioselectivity. Specifically, Heck insertion stereodetermining step to form ƞ³ π-allyl complex situ trapping nucleophiles enable Heck/etherification formal (4+2) cycloaddition manner. Engineering Sadphos bearing androgynous non-C₂-symmetric chiral sulfinamide phosphine ligands vital component achieving catalytic reactivity This strategy offers general, modular divergent platform rapidly upgrading feedstock dienes various value-added molecules is expected inspire development other Heck/cross-couplings.

Язык: Английский

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Nickel-Catalyzed Atroposelective Reductive [2 + 4] Annulation toward Synthesis of Axially Chiral Biaryls

ACS Catalysis, Год журнала: 2024, Номер 14(22), С. 17039 - 17045

Опубликована: Ноя. 4, 2024

Herein, we demonstrate the successful application of reductive [2 + 4] annulation in atroposelective de novo benzene ring formation. This nickel-catalyzed reaction between β-substituted α-naphthylalkynes and a biselectrophile C(sp2)–X type offers an efficient convenient method to prepare highly enantioenriched C1-symmetric axially chiral biaryls containing two preinstalled functionalities. The coupling products can be used as versatile synthetic intermediates access bidentate ligands or bifunctional organocatalysts, their utility asymmetric catalysis is also showcased this context.

Язык: Английский

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Access to Azacycles by Cobalt-Catalyzed Asymmetric Cross-Electrophile Coupling

Synfacts, Год журнала: 2023, Номер 19(10), С. 1006 - 1006

Опубликована: Сен. 14, 2023

Key words azacycles - cobalt catalysis cross-electrophile coupling nonconjugated iododienes

Язык: Английский

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Reductive Dicarbofunctionalization of C–C π-Bonds

Elsevier eBooks, Год журнала: 2023, Номер unknown

Опубликована: Янв. 1, 2023

Язык: Английский

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