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Asymmetric Binary‐Acid Catalysis with InBr 3 in the Inverse‐Electron‐Demanding Hetero‐Diels–Alder Reaction of Mono‐ and Bis‐Substituted Cyclopentadienes: Remote Fluoro‐Effect on Stereocontrol
Author(s) -
Lv Jian,
Zhang Long,
Hu Shenshen,
Cheng JinPei,
Luo Sanzhong
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103340
Subject(s) - phosphoric acid , regioselectivity , substituent , catalysis , stereoselectivity , binary number , inverse , scheme (mathematics) , diastereomer , chemistry , diels–alder reaction , combinatorial chemistry , organic chemistry , computer science , mathematics , arithmetic , mathematical analysis , geometry
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 (see scheme).