DOI: 10.1021/acs.orglett.6c04395 ISSN: 1523-7060
Protease-Catalyzed Aldol Condensation To Access Axially and Centrally Chiral Biaryls
Hai-Bo Cui, Ying-Ting Ma, Hua Wan, Dan Liu, Wei-Qin Liu, Zheng-Yi Tang, Zhi-Rui Wang, Jie Yang, Ya Lv, Hai-Long Yan, Yong-Zheng ChenAbstract
Asymmetric synthesis of axially chiral biaryls with multiple stereogenic elements remains challenging. Herein, we report an enzymatic asymmetric aldol condensation via desymmetrization that constructs carbon-centered stereocenters and biaryl axes simultaneously. This biocatalytic strategy affords a range of atropisomers with high diastereo- and enantioselectivities (up to >99:1 er and >19:1 dr). The protocol operates at high substrate loadings under mild conditions and tolerates a range of substrates, giving products containing both axial and central chirality.