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Asymmetric synthesis via heteroconjugate addition using Eliel's camphor template
Affiliation:1. ADINACO Research Group, Department of Pharmaceutical Botany, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic;2. Department of Bioorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic;3. Department of Toxicology and Military Pharmacy, Trebesska 1575, 500 05 Hradec Kralove, Czech Republic;4. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 500 05 Hradec Kralove, Czech Republic;5. Department of Pharmacognosy, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic;6. Department of Chemistry, Faculty of Science, University of Hradec Kralove, Rokitanskeho 62, 500 03 Hradec Kralove, Czech Republic;7. Department of Analytical Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic;1. Instituto Universitario de Enfermedades Tropicales y Salud Pública de Canarias, Universidad de La Laguna, Avda. Astrofísico Fco. Sánchez, S/N, 38203 La Laguna, Tenerife, Islas Canarias, Spain;2. Departamento de Obstetricia y Ginecología, Pediatría, Medicina Preventiva y Salud Pública, Toxicología, Medicina Legal y Forense y Parasitología, Universidad de La Laguna, Tenerife, Spain;3. Red de Investigación Colaborativa en Enfermedades Tropicales (RICET), Instituto de Salud Carlos III, Madrid, Spain;4. Instituto Universitario de Bio-Orgánica ‘Antonio González’, Departamento de Química Orgánica, Universidad de La Laguna, Avda. Fco. Sánchez 2, 38206 La Laguna, Tenerife, Islas Canarias, Spain;5. Centro Atlántico del Medicamento S.A (CEAMED S.A.), PCTT, La Laguna, Tenerife, Islas Canarias, Spain;1. Department of Chemistry, Tsinghua University, Beijing 100084, China;2. Materials Research Laboratory, University of California, Santa Barbara, Santa Barbara, CA 93106, USA;1. Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan;2. ACT-C, Japan Science and Technology Agency (JST), Sapporo 060-0812, Japan
Abstract:A new asymmetric synthesis is reported that includes carbon—carbon bond formation based upon heteroconjugate addition with Eliel's 1R-(+)-camphor derivative as a template. This method showed high enantiomeric excess under chelation control affected by the solvent polarity and by the salt present in the reaction media. (+)-Citronellal was synthesized as a proof of this method.
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