Asymmetric Organocatalytic N-Alkylation of Indole-2-carbaldehydes with α,β-Unsaturated Aldehydes: One-Pot Synthesis of Chiral Pyrrolo[1,2-a]indole-2-carbaldehydes

✍ Scribed by Liang Hong; Wangsheng Sun; Chunxia Liu; Lei Wang; Rui Wang

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 267 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200902638

✦ Synopsis

The pyrroloA C H T U N G T R E N N U N G [1,2-a]indole tricyclic ring structures are widely presented in a number of naturally occurring products and have attracted much attention due to the broad scope of their biological activities. [1] Representative examples are mitomycins, [1b] some of the most effective antitumor agents, and yuremamine, [1f] a new phytoindole recently isolated from the stem bark of Mimosa hostilis, which shows hallucinogenic and psychoactive effects. In addition to being an important motif in many biologically and pharmaceutically interesting compounds, they are also useful intermediates for the synthesis of polyheterocycles. [2] Although several approaches for the synthesis of this system have been explored, they usually require several steps and expensive reagents. [3] Thus, the exploration of novel, concise methodologies that allow the rapid establishment of these polycyclic indole skeletons in a single operation is highly desired. [4] [a] Dr.