Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 23, Pages 5238-5250Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1590931
Keywords
amino acids; chiral pool; esterification; indium; oxazoles; photochemistry; thiourea; thioxanthone
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Funding
- European Research Council under the European Union's Horizon 2020 research and innovation programme [665951 - ELICOS]
- Alexander von Humboldt-Stiftung
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Four different 1-aminocyclohexanes bearing a tethered thioxanthone group in the 2-position were prepared. The synthesis commenced with the respective N-protected beta-amino acids, the carboxyl group of which was employed for the introduction of the thioxanthone moiety. After construction of the thioxanthone and protecting group removal, the conversion of the amino group into the respective thiourea was accomplished by treatment with N-3,5-bis(trifluoromethyl) phenyl isothiocyanate and yielded the title compounds in which the thioxanthone resides in different spatial positions relative to the thiourea motif. Overall yields varied between 20-35%.
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