Michael addition of nitroalkanes to nonactivated α,β-unsaturated δ-thiolactams: reactivity, diastereoselectivity, and comparison to α,β-unsaturated δ-lactams |
| |
Authors: | Jacek G So?nicki |
| |
Institution: | Szczecin University of Technology, Institute of Chemistry and Environmental Protection, Al. Piastów 42, PL-71065 Szczecin, Poland |
| |
Abstract: | Aliphatic nitrocompounds add to nonactivated α,β-unsaturated δ-thiolactams leading to 4-nitroalkyl functionalized δ-thiolactams in good yields. The addition is a stereocontrolled process with respect to substituents at C-6, and takes place producing trans 4,6-disubstituted adducts in most cases. Ease of the addition has been studied in relation to the structure of the δ-thiolactam acceptors, within the FMO-theory. Comparative study with analogous δ-lactams has shown the advantages of α,β-unsaturated δ-thiolactams in Michael addition and indicated high prospects of these compounds in the synthesis of 4-functionalized piperidine derivatives. |
| |
Keywords: | Michael addition Nitroalkanes Reactivity Diastereoselectivity α β-Unsaturated δ-(thio)lactams 5 6-Dihydro-1H-pyridine-2-(thi)one 4-Nitroalkylpiperidine-2-(thi)ones FMO-theory |
本文献已被 ScienceDirect 等数据库收录! |
|