278593-54-7Relevant academic research and scientific papers
Cascading single-step stereoselective construction of the α-alloyohimbine framework: A new synthesis of (-)-nitraraine
Sakagami, Hideki,Ogasawara, Kunio
, p. 43 - 47 (2007/10/03)
(-)-Nitraraine and its 10-methoxy -analogue having an α-alloyohimbine framework have been constructed stereoselectively in a cascading single step sequence from chiral mono-substituted N-2-(3-indolyl)ethyltetrahydropyridine precursors under the Heck react
Lipase-mediated synthesis of enantiopure N-carbobenzoxy-3-hydroxy- 1,2,3,4-tetrahydro- and N-carbobenzoxy-3-hydroxy-1,2,3,6-tetrahydropyridines from 3-hydroxypyridine
Sakagami, Hideki,Ogasawara, Kunio
, p. 521 - 524 (2007/10/03)
Two isomeric chiral hydroxytetrahydropyridines, having high potential utility for the construction of a variety of chiral amine derivatives, have been prepared in both enantiomeric forms by employing lipase-mediated resolution starting from 3-hydroxypyridine. Thus, on exposure to sodium borohydride in the presence of carbobenzoxy chloride, 3-hydroxypyridine has been found to furnish racemic N-carbobenzoxy-3-hydroxy-1,2,3,4- tetrahydropyridine, which is resolved under trans-esterification conditions in the presence of lipase PS to give both enantiomeric products in enantiopure forms. Isomerization of the chiral 1,2,3,4-tetrahydro-product into the chiral 1,2,3,6-tetrahydro-derivative has been accomplished without loss of the original chiral integrity. The racemic 1,2,3,6-tetrahydro- derivative has also been resolved under the same lipase-mediated trans- esterification conditions.
