A One-Pot Cross-Metathesis/Allylboration Reaction: A Three-Component Coupling for the Synthesis of Functionalized Homoallylic Alcohols

✍ Scribed by Steven D. Goldberg; Robert H. Grubbs

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 87 KB
• Volume: 114
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3757(20020301)114:5<835::aid-ange835>3.0.co;2-7

✦ Synopsis

General procedure: A flame-dried round-bottomed flask was charged with 4 (1 equiv) and the olefin cross partner (3.0 equiv). A rubber septum was attached, dichloromethane was added (0.2 ± 0.3 n in 4), and argon was bubbled through the resultant solution for 10 min. Under a stream of argon, 3 (0.050 equiv) was added to the degassed solution as a solid. A reflux condenser was attached immediately, and the entire system was flushed with argon for 2 min. The colored solution was then heated at reflux for 2 ± 12 h, and the reaction was monitored by thin-layer chromatography. Upon consumption of 4, the aldehyde (1.5 equiv) was added to the reaction mixture through a syringe, and the resultant solution was stirred at 23 8C for 12 ± 48 h. The solution was concentrated in vacuo, and the residue was purified by means of silica gel chromatography to afford 6. Characterization data for 6 a ± 6 l are given in the Supporting Information.