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Unusual Ester‐Directed Regiochemical Control in endo ‐Selective Asymmetric 1,3‐Dipolar Cycloadditions of Azomethine Ylides with β‐Sulfonyl Acrylates
Author(s) -
Tong MinChao,
Li Jun,
Tao HaiYan,
Li YuXue,
Wang ChunJiang
Publication year - 2011
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.201102430
Subject(s) - regioselectivity , sulfonyl , chemistry , cycloaddition , 1,3 dipolar cycloaddition , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , catalysis , alkyl
Ester‐controlled regioselectivity! A highly efficient, asymmetric 1,3‐dipolar cycloaddition of azomethine ylides with unsymmetrically 1,2‐diactivated sulfonylacrylates has been developed, accompanied by an unusual regioselectivity that is controlled by the ester group rather than the sulfonyl group (see scheme). Theoretical calculations revealed a stepwise mechanism and rationalized the unusual ester‐directed regioselectivity.