The rare cis-configured trisubstituted lactam products obtained by the Castagnoli–Cushman reaction in N, N-dimethylformamide. Issue 55 (18th May 2016)

• Record Type: Journal Article
• Authors: Dar'in, Dmitry; Bakulina, Olga; Nikolskaya, Sofia; Gluzdikov, Ivan; Krasavin, Mikhail
• Is Part Of: RSC advances. Volume 6:Issue 55(2016)
• Page Start: 49411
• Page End: 49415
• Publication Date: 2016-05-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra10249b
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Unlike its trans counterpart, the cis -configured scaffold derived from the Castagnoli–Cushman reaction (CCR) is scarce and has not been explored in bioactive compound design. Abstract : Unlike its trans counterpart, the cis -configured scaffold derived from the Castagnoli–Cushman reaction (CCR) is scarce and has not been explored in bioactive compound design. We found that conducting this reaction in DMF (in contrast to conventional toluene or xylene) led to a significantly higher proportion of cis -configured lactams in the diastereomeric product mixture. This allowed us, for the first time, to obtain and thoroughly characterize both stereoisomers of a significant number of lead-like CCR lactams. Simple rules for 1 H NMR-based stereochemical assignment have been devised and correlated with the single-crystal X-ray structures obtained for pure cis - and trans -configured lactams.