Asymmetric binary-acid catalysis with InBr3 in the inverse-electron-demanding hetero-Diels-Alder reaction of mono- and bis-substituted cyclopentadienes: remote fluoro-effect on stereocontrol |
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| Authors: | Lv Jian Zhang Long Hu Shenshen Cheng Jin-Pei Luo Sanzhong |
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| Institution: | Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, the Chinese Academy of Sciences, Beijing 100190, PR China. |
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| Abstract: | Remote F effect: Unprecedented hetero-Diels-Alder reactions of mono- and bis-substituted cyclopentadienes have been realized by an asymmetric binary-acid catalyst that synergistically combines a chiral phosphoric acid 1?h/InBr(3) with good periselectivity, high regioselectivity, and excellent stereoselectivity. Substituent mapping of the chiral phosphoric acid indicates a dramatic remote ortho-fluoro effect on the stereocontrol. |
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| Keywords: | asymmetric catalysis fluorine hetero‐Diels–Alder reaction indium bromide substituted cyclopentadienes regioselectivity |
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