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

Article abstract of DOI:10.1016/0040-4039(94)02216-X

The 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.