646512-46-1Relevant academic research and scientific papers
A practical procedure for the synthesis of multifunctional aldehydes through the Fukuyama reduction and elucidation of the reaction site and mechanism
Kimura, Mayumi,Seki, Masahiko
, p. 3219 - 3223 (2007/10/03)
A highly efficient heterogeneous Pd/C catalyst D1 was found to effect the reduction of thiol esters 1 to the corresponding aldehydes 2 with such a low catalyst loading as 0.5-1.0mol%. The chemical properties of the Pd/C catalysts together with the XRF analysis reveal that the reduction is most likely to proceed on the solid surface of the Pd/C catalyst rather than in the solution phase outside the pores. A reaction mechanism through oxidative addition of Pd to the thiol esters 1 was postulated by detection of the oxidative addition intermediate by React IR analysis. A practical purification of 2 was accomplished by conversion to water-soluble bisulfite adducts 7.
A Facile Synthesis of a Key Intermediate for (+)-Biotin via Strecker Reaction
Mori, Yoshikazu,Kimura, Mayumi,Seki, Masahiko
, p. 2311 - 2316 (2007/10/03)
The Strecker reaction of (2R,4R)-2-phenyl-3-phenoxycarbonylthiazolidine-4- carbaldehyde (4b), which was readily prepared from L-cysteine, with benzylamine and trimethylsilyl cyanide provided α-amino nitrile 5b stereoselectively (syn-anti, 2:1), Amidation of 5b and subsequent cyclization gave bicyclic compound 6, which, upon reduction with zinc dust, hydrolysis and subsequent cyclization, furnished thiolactone 2, a key intermediate for (+)-biotin (1).
