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Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3+3] Cycloaddition Reaction for the Formation of Enantioenriched Piperidines
Author(s) -
Hayashi Yujiro,
Gotoh Hiroaki,
Masui Ryouhei,
Ishikawa Hayato
Publication year - 2008
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.200800662
Subject(s) - enantioselective synthesis , cycloaddition , catalysis , chemistry , isomerization , piperidine , silyl ether , hydrolysis , silylation , ether , ene reaction , organic chemistry
Aza‐ene reaction : Diphenylprolinol silyl ether was found to be an effective organocatalyst for the formal aza [3+3] cycloaddition reaction of α,β‐unsaturated aldehydes and enecarbamates (see scheme). The reaction proceeds through an asymmetric catalytic ene reaction, isomerization, hydrolysis, and cyclization to afford piperidine derivatives in good yields and excellent enantioselectivities.