Tetrahedron

Stereoselective alkylation of N-Boc-2-pyrrolidinones and N-Boc-2-piperidinones. Synthesis and characterization of disubstituted lactams

AO Maldaner, RA Pilli

Index: Maldaner, Adriano O.; Pilli, Ronaldo A. Tetrahedron, 1999 , vol. 55, # 47 p. 13321 - 13332

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Citation Number: 22

Abstract

Alkylation of enolates of monosubstituted N-Boc lactams 4–6 afforded trans-disubstituted lactams as the major isomer. In the pyrrolidinone series, 1, 3-induction seems to be ruled by steric interactions and the diastereoselection is low for the alkylation of enolates with small substituents at C-5 (eg, Me) and methyl iodide. The trans selectivity improves with bulkier substituents at C-2 and/or bulkier electrophiles. The formation of 3, 6-trans-disubstituted ...