Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 21, Pages 3865-3879Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700879
Keywords
Synthetic methods; C-C coupling; Cross-coupling; Synthesis design; Ti-Claisen condensation; Suzuki-Miyaura cross-coupling; Negishi cross-coupling; Sonogashira cross-coupling; strobilurin A
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) [18350056, 17035087, 18037068, 15K05508, 17655045]
- Grants-in-Aid for Scientific Research [15K05508, 17K14488] Funding Source: KAKEN
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TiCl4-Et3N or -Bu3N reagent conducted a highly (Z)-stereoselective carbon homologation (dehydration type Ti-Claisen condensation) of alkyl alpha-heteroatom (halo and sulfonyloxy)-substituted acetates (XCH2CO2R) with alkyl formates (HCO2R) to afford various alkyl beta-alkoxy-alpha-halo or sulfonyloxy-substituted acrylates (24 examples; 51%-91% yield). Stereoretentive Suzuki-Miyaura, Negishi, and Sonogashira cross-couplings using the obtained methyl beta-methoxy-alpha-halo or sulfonyloxy-substituted acrylates proceeded smoothly to produce a variety of beta-alkoxy-alpha-substituted acrylates in moderate to high yield (35 examples; 29%-99% yield). As a successful application, a 3-step straightforward synthesis of strobilurin A was performed utilizing the present reaction sequence (dehydration type Ti-Claisen condensation and Suzuki-Miyaura crosscoupling), wherein the geometry of the three consecutive olefins (2E,3Z,5E) was completely maintained.
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