Thermodynamic equilibration in Pd(0)-catalyzed interconversion of highly constrained [2.1.2] bicyclic lactones: its mechanistic investigation |
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Authors: | Young Taek Han Sujin Lee Jae-Kyung Jung Jeeyeon Lee |
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Institution: | a College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea b College of Pharmacy, Chungbuk National University, Cheongju 361-763, Republic of Korea c College of Pharmacy, Woosuk University, Wanju, 565-701, Republic of Korea |
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Abstract: | Mechanistic study on the stereoselective construction of 2.1.2] bicyclic lactone skeleton via Pd(0)-catalyzed intramolecular allylic alkylation was described. The observed excellent stereoselectivity is likely due to Pd(0)-catalyzed equilibration of highly strained 2.1.2] bicyclic lactone framework via π-σ-π isomerization of π-allylpalladium complex. An efficient synthetic route to allylic carbonate as a requisite cyclization precursor has also been developed by employing a sequence of ring-closing metathesis, followed by epoxidation/desilylation of the resulting substituted oxasilepene intermediate. |
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