Collect. Czech. Chem. Commun.
2008, 73, 705-732
https://doi.org/10.1135/cccc20080705
Preparation of Boc-Protected Cinnamyl-Type Alcohols: A Comparison of the Suzuki-Miyaura Coupling, Cross-Metathesis, and Horner-Wadsworth-Emmons Approaches and Their Merit in Parallel Synthesis
Jan Štambaský, Andrei V. Malkov* and Pavel Kočovský*
Department of Chemistry, WestChem, University of Glasgow, Glasgow G12 8QQ, U.K.
Abstract
Three synthetic strategies for the construction of tert-butyl (E)-3-arylprop-2-en-1-ol carbonates are described. Complementary approaches employing Suzuki-Miyaura coupling and cross-metathesis reaction gave moderate yields of the title compounds in one-step, both methods are suitable for high-throughput and parallel chemistry. A detailed investigation into the Suzuki-Miyaura coupling reaction is provided along with the studies on the synthesis of pinacolyl 1-(tert-butyloxycarbonyl)propenol-3-ylboronate, the key building block. Conventional synthesis of the title compounds via the Horner-Wadsworth-Emmons reaction as a key step in a three-step-one-purification protocol was optimized and the results are compared with those of the latter reactions.
Keywords: C-C bond formation; Palladium; Ruthenium; Suzuki-Miyaura reaction; Metathesis.
References: 63 live references.
