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Convenient Titanium(III)‐Catalyzed Synthesis of Cyclic Aminoketones and Pyrrolidinones—Development of a Formal [4+1] Cycloaddition
Author(s) -
Frey Georg,
Luu HieuTrinh,
Bichovski Plamen,
Feurer Markus,
Streuff Jan
Publication year - 2013
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.201302460
Subject(s) - cycloaddition , imine , nitrile , catalysis , chemistry , titanium , yield (engineering) , carbon fibers , combinatorial chemistry , computer science , organic chemistry , materials science , algorithm , metallurgy , composite number
Have it both ways : α‐Aminated ketones can be prepared by the titanium(III)‐catalyzed reductive radical cyclization of iminonitriles. Depending on the position of the nitrile at the imine carbon or nitrogen, cyclic aminoketones or pyrrolidin‐3‐ones with a tetrasubstituted α‐carbon can be formed in up to quantitative yield. In the latter case, the imine condensation and Ti III catalysis correspond to a formal [4+1] cycloaddition.