Phosphine-Catalyzed Asymmetric Allylic Alkylation of Achiral MBH Carbonates with 3,3′-Bisindolines: Enantioselective Construction of Quaternary Stereogenic Centers

The asymmetric allylic alkylation (AAA) of achiral Morita-Baylis-Hillman (MBH) carbonates with 3,3'-bisindolines under the catalysis of amino-acid-derived bifunctional phosphines was accomplished. With the AAA approach introduced herein, challenging 3,3'-bisindolines bearing an all-carbon quaternary stereocenter (C3a) have been constructed in good yields with good to excellent enantioselectivties. In addition, the synthetic value of this protocol was demonstrated by the facile synthesis of the core skeleton of gliocladin C.

Automated summary

The asymmetric allylic alkylation of achiral Morita-Baylis-Hillman (MBH) carbonates with 3,3'-bisindolines using amino-acid-derived bifunctional phosphines as catalysts has been achieved, resulting in the construction of challenging 3,3'-bisindolines with an all-carbon quaternary stereocenter (C3a) in good yields and excellent enantioselectivities. Furthermore, the synthetic utility of this method was demonstrated by facilely synthesizing the core skeleton of gliocladin C.