18631-96-4Relevant articles and documents
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Schenker,Prelog
, p. 896,898 (1953)
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Carbon-carbon bond formation by electrochemical catalysis in conductive microemulsions
Gao, Jianxin,Rusling, James F.,Zhou, De-Ling
, p. 5972 - 5977 (2007/10/03)
Bicontinuous microemulsions made from oil, water, and surfactants were examined as substitutes for organic solvents in carbon-carbon bond-forming reactions. Conjugated additions of primary alkyl iodides 3a-c to 2-cyclohexen-1-one (4) to give 3-alkyl cyclohexanones 5a-c and cyclization of 2-(4-bromobutyl)-2-cyclohexen-1-one (9) to 1-decalone (10) were mediated by the Co(I)L complex vitamin B12s generated at carbon cloth electrodes under mild conditions. Reaction of the Co(I)L nucleophile with the alkyl halides gives a Co-alkyl complex. Cleavage of the Co-alkyl complexes by using an electrode potential of -0.85 V (all vs SCE) and irradiation with visible light, or a potential of -1.45 V in the dark, were compared. Addition of the resulting alkyl radicals to the activated double bonds gave comparable yields of 3-alkylcyclohexanone 5a-c (70-80% using -0.85 V + light) and 1-decalone (90%, both cleavage modes) 10 in microemulsions and in DMF. Microemulsions containing hexadecyltrimethylammonium bromide (CTAB) gave remarkable stereoselectivity for the trans isomer of 10, while homogeneous DMF and a sodium dodecylsulfate (SDS) microemulsion gave little stereoselectivity.
The role of proline in the asymmetric step of the Woodward synthesis of erythromycin
Agami,Platzer,Puchot,Sevestre
, p. 1091 - 1098 (2007/10/02)
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