Collect. Czech. Chem. Commun. 2008, 73, 705-732

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.


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.