Publication: The morita-baylis-hillman reaction of chiral highly oxygenated cyclopent-2-enones
Issued Date
2012-10-01
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ISSN
15222675
0018019X
0018019X
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2-s2.0-84867706563
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Mahidol University
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SCOPUS
Bibliographic Citation
Helvetica Chimica Acta. Vol.95, No.10 (2012), 1912-1927
Suggested Citation
Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Chaveng Pakawatchai, Vichai Reutrakul, Manat Pohmakotr The morita-baylis-hillman reaction of chiral highly oxygenated cyclopent-2-enones. Helvetica Chimica Acta. Vol.95, No.10 (2012), 1912-1927. doi:10.1002/hlca.201200421 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/13601
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Title
The morita-baylis-hillman reaction of chiral highly oxygenated cyclopent-2-enones
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Abstract
The Morita-Baylis-Hillman (MBH) reactions of (4S,5R,7R,8R)- and (4R,5R,7R,8R)-4-hydroxy-7,8-dimethoxy-7,8-dimethyl-6,9-dioxaspiro[4.5] dec-2-en-1-ones (2 and 3, resp.) with aldehydes using various catalysts were studied. A combination of Bu 3 P/phenol in THF was found being optimum conditions giving the corresponding MBH adducts with high diastereoisomeric ratios. After separation, each stereomerically pure isomer of the MBH adducts was subjected to hydrolysis employing 1% aq. CF 3 COOH (TFA) in a water bath of an ultrasonic cleaner to afford the corresponding polyhydroxylated cyclopentenones in good yields. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.