Synthesis of β-halobutenolides and their Pd(0)-catalyzed cross-coupling reactions with terminal alkynes and organozinc reagents. A general route to β-substituted butenolides and formal synthesis of cis-whisky lactone

✍ Scribed by Shengming Ma; Zhangjie Shi; Zhanqian Yu

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 654 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00726-7

✦ Synopsis

An improved procedure for the efficient synthesis of I~-halobutenolides was developed. The Pd(0)catalyzed coupling reactions of 13-halobutenolides with terminal alkynes or organozinc reagents, i.e., 1-alkenyl, aryl, and alkyl zinc reagents, to afford 13-substituted butenolides were carefully studied. Using the coupling protocol of T-(n-butyl)-13-iodobutenolide with methylzinc halide, we performed an efficient formal synthesis of whisky lactone.