Tetrahedron Letters p. 1575 - 1578 (1999)
Update date:2022-08-03
Topics:
Ezquerra, Jesus
Prieto, Lourdes
Avendano, Carmen
Martos, Jose Luis
De La Cuesta, Elena
Ethyl 4,4-dimethylpyroglutamate has been used as a chiral auxiliary for α,β-unsaturated acids in Michael addition reactions. The conjugate addition of Grignard reagents to the amides in the presence of copper iodide, tetramethylene diamine (TMEDA) and trimethylsilyl chloride, proceeded with high yields and excellent stereoselectivities, yielding after hydrolysis enantiomerically pure β-substituted carboxylic acid derivatives.
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