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One‐Pot Tandem 1,4–1,2‐Addition of Phosphites to α,β‐Unsaturated Imines for the Synthesis of Glutamic Acid Analogues
Author(s) -
Moonen Kristof,
Van Meenen Ellen,
Verwée Annelies,
Stevens Christian V.
Publication year - 2005
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.200501830
Subject(s) - tandem , trimethylsilyl , chemistry , combinatorial chemistry , organic chemistry , stereochemistry , materials science , composite material
Evidently so : New mechanistic findings indicate that addition of dialkyl trimethylsilyl phosphites to α,β‐unsaturated imines has been incorrectly reported as an exclusive 1,2‐addition. When α,β‐unsaturated imines are used as substrates, 1‐alkylamino 3‐phosphonyl phosphonates are formed in high yields in the presence of a suitable proton source through a sequential 1,4‐ and 1,2‐addition.