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Catalytic Divergent [3+3]‐ and [3+2]‐Cycloaddition by Discrimination Between Diazo Compounds
Author(s) -
Deng Yongming,
Massey Lynée A.,
Rodriguez Núñez Yeray A.,
Arman Hadi,
Doyle Michael P.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706639
Subject(s) - cycloaddition , regioselectivity , diazo , catalysis , chemistry , acetonitrile , medicinal chemistry , azepine , tetrafluoroborate , copper , ylide , organic chemistry , ionic liquid
Highly selective divergent cycloaddition reactions of enoldiazo compounds and α‐diazocarboximides catalyzed by copper(I) or dirhodium(II) have been developed. With tetrakis(acetonitrile)copper(I) tetrafluoroborate as the catalyst epoxypyrrolo[1,2‐a]azepine derivatives were prepared in good yields and excellent diastereoselectivities through the first reported [3+3]‐cycloaddition of a carbonyl ylide. Use of Rh 2 (pfb) 4 or Rh 2 (esp) 2 directs the reactants to regioselective [3+2]‐cycloaddition generating cyclopenta[2,3]pyrrolo[2,1‐b]oxazoles with good yields and excellent diastereoselectivities.