Enantiodivergent synthesis of trans-3,4-disubstituted succinimides by SmI2-mediated Reformatsky-type reaction

✍ Scribed by Geng-Jie Lin; Shi-Peng Luo; Xiao Zheng; Jian-Liang Ye; Pei-Qiang Huang

• Book ID: 104095348
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 144 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.04.090

✦ Synopsis

An enantiodivergent strategy for the synthesis of trans-3,4-disubstituted succinimides is reported. The key step is a highly transstereoselective SmI 2 -induced Reformatsky-type reaction of 4-substituted-O-benzoylated malimides with carbonyl compounds. Double chirality transmissions were performed with good to excellent diastereoselectivities.