462068-88-8Relevant articles and documents
Highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl esters via Sc(OTf)3-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines
Pohmakotr, Manat,Yotapan, Nattawut,Tuchinda, Patoomratana,Kuhakarn, Chutima,Reutrakul, Vichai
, p. 5016 - 5019 (2007)
(Chemical Equation Presented) Functionalized γ-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of β-carboxy-γ-lactams and their ethyl este
1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines
Chupakhin, Evgeny G.,Bakulina, Olga Yu.,Dar'in, Dmitry V.,Krasavin, Mikhail
, p. 292 - 293 (2019/06/13)
A novel protocol for the Castagnoli–Cushman reaction of dicarboxylic acids and imines comprises the use of 1,1′-carbonyldiimidazole as the cyclodehydrating agent to in situ produce the intermediate anhydrides. In contrast to previously developed procedure
The rare: Cis -configured trisubstituted lactam products obtained by the Castagnoli-Cushman reaction in N, N -dimethylformamide
Dar'In, Dmitry,Bakulina, Olga,Nikolskaya, Sofia,Gluzdikov, Ivan,Krasavin, Mikhail
, p. 49411 - 49415 (2016/06/15)
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 1H NMR-based stereochemical assignment have been devised and correlated with the single-crystal X-ray structures obtained for pure cis- and trans-configured lactams.