A simple preparation of (R)-(2-cyclopentenyl)acetic acid and (R)-(2-cyclohexenyl)acetic acid using β-diastereoselective radical cyclization in the presence of Lewis acid
1995; Elsevier BV; Volume: 36; Issue: 2 Linguagem: Inglês
10.1016/0040-4039(94)02216-x
ISSN1873-3581
AutoresMayumi Nishida, Hiroshi Hayashi, Yousuke Yamaura, Emi Yanaginuma, Osamu Yonemitsu, Atsushi Nishida, Norio Kawahara,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe alkenyl radical generated from (−)-8-phenylmenthyl 7-iodo-2,6-heptadienoate smoothly cyclized to afford (R)-(2-cyclopentenyl)acetate with 88% de in 90% yield. (R)-(2-Cyclohexenyl)acetate was also obtained with 84% de in 72% yield under the same conditions. The presence of Lewis acid is essential for high diastereoselectivity and chemical yield.
Referência(s)