Cyanosilylation at pregnane side-chains. Selective synthesis and crystal structure of 20(R)-silylated cyanohydrins |
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| Authors: | Cruz Silva M Manuel Andrade Lourdes C R Paixão José A de Almeida M José e Melo M Luisa Sá |
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| Affiliation: | Centro de Estudos Farmacêuticos, Lab. Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, Coimbra 3000, Portugal. |
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| Abstract: | Trimethylsilylcyanide addition to different carbonyl moieties, i.e. saturated ketones, an enone and an aldehyde, at the steroid side-chain, was studied in the presence of a convenient catalyst. Depending on the nature of the carbonyl group, different outcomes were noticed. Saturated 20-keto pregnanes yielded epimerically pure silylated cyanohydrins, being the absolute configuration unambiguously established by X-ray crystallographic analysis. |
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| Keywords: | Cyanohydrins Stereoselectivity Steroids Pregnanes TMSCN X-Ray |
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