Document Detail


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.
MedLine Citation:
PMID:  22170757     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Jian Lv; Long Zhang; Shenshen Hu; Jin-Pei Cheng; Sanzhong Luo
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-14
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-15     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, the Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-62554449.
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