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

Stambasky, J., Malkov, A. V. and Kocovsky, P. (2008) 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. Collection of Czechoslovak Chemical Communications, 73(5), pp. 705-732. (doi: 10.1135/cccc20080705)

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.

• Item Type: Articles
• Keywords: ACETATES ALCOHOLS ARYL CHLORIDES C-C bond formation Carbonates CATALYZED ALLYLIC ALKYLATION CHEMISTRY Cross metathesis DERIVATIVES ESTERS high-throughput LIGANDS METATHESIS Palladium REAGENTS ruthenium STEP STRATEGIES STRATEGY SUBSTITUTION Suzuki-Miyaura reaction TERT-BUTYL DICARBONATE
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Malkov, Dr Andrei and Kocovsky, Professor Pavel
• Authors: Stambasky, J., Malkov, A. V., and Kocovsky, P.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Collection of Czechoslovak Chemical Communications
• ISSN: 0010-0765