Issue 8, 1999

The synthesis of α-amino-γ-substituted adipic acids: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate

Abstract

The α,β-unsaturated lactam 3 was submitted to 1,4-addition of organocuprate reagents R2CuLiI2 (R = Me, Bu or Ph) to provide the 4-substituted compounds 5a–c, 6a–c as a mixture of diastereomers; these intermediates were then transformed into the corresponding α-amino-γ-substituted adipic acids 7a–c, 8a–c.

Article information

Article type
Paper

Chem. Commun., 1999, 683-684

The synthesis of α-amino-γ-substituted adipic acids: stereoelectronic effects during the 1,4-addition of organocuprates to methyl N-tert-butoxy-6-oxo-1,2,3,6-tetrahydropyridine-2-carboxylate

M. Muller, A. Schoenfelder, B. Didier, A. Mann and C. Wermuth, Chem. Commun., 1999, 683 DOI: 10.1039/A809274E

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