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

✍ Scribed by Adriano O. Maldaner; Ronaldo A. Pilli

Book ID
104209698
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
615 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

Alkylation of Β’nolates of mcvvsubstituted N-BOc Iactams 4-6 afforded trans-disubstituted lactams as the major is~ner. In the pyrrolidinonΒ’ sa'ies, 1,3-induction seems to be ruled by stetic interacti~s and the diasterc~electi~m is low fcΒ’ the alkylation of enolates with small substitumts at C-5 (e.&, Me) and methyl iodide. The tram selectivity imwoves with bulkier substi~ts at C-2 and/or bulkier electro,lies. The formation of 3,6-trans-disubstituted piperidinc~les benefits from the axial orientation of the substituent at C-2 due to the A L3 su~ with the N-BOc group and excellent trans preference is observed even in the alkylatic~ of the lithium enolate of N-Boc-6-methyl piperidinone with methyl iodide.

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ChemInform Abstract: Stereoselective Alk
ChemInform Abstract: Stereoselective Alkylation of N-Boc-2-pyrrolidinones and N-Boc-2-piperidinones. Synthesis and Characterization of Disubstituted Lactams.
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