Asymmetric synthesis of chromans via the Friedel-Crafts alkylation-hemiketalization catalysed by an N,N '-dioxide scandium(III) complex

作者：Hao, Xiaoyu; Lin, Lili^*; Tan, Fei; Ge, Shulin; Liu, Xiaohua; Feng, Xiaoming^*

来源：Organic Chemistry Frontiers, 2017, 4(8): 1647-1650.

DOI：10.1039/c7qo00323d

• COMBINATORIAL LIBRARIES
• PRIVILEGED STRUCTURES
• ENANTIOSELECTIVE SYNTHESIS
• EFFICIENT SYNTHESIS
• ALPHA-TOCOPHEROL
• CASCADE REACTION
• CHEMISTRY
• ACCESS
• SALICYLALDEHYDES
• CYCLOADDITION

An enantioselective tandem Friedel-Crafts alkylation-hemiketalization between electron-rich phenols and alpha,beta-unsaturated ketoesters gave a direct approach to chiral 2,3-disubstituted chromans in the presence of a chiral N,N'-dioxide/Sc(OTf)(3) complex. High enantioselectivities (up to 95% ee), high diastereoselectivities (up to 14 : 1) and high yields (up to 97%) were obtained for a broad range of substrates under mild reaction conditions.

• 出版日期2017-8-1
• 单位四川大学