1.
J Org Chem
; 79(7): 3238-43, 2014 Apr 04.
Article
in English
| MEDLINE
| ID: mdl-24641577
ABSTRACT
Adenosine-derived ketone 5 was subjected to Noyori asymmetric transfer hydrogenation (ATH) using aqueous sodium formate as a stoichiometric reductant. Despite the well-known sensitivity of ATH to stereoelectronic effects from a contiguous stereogenic center, the 5' stereochemistry was overwhelmingly controlled by the chirality of the catalyst. Both the (5'S,4'R) and the (5'R,4'R) diastereomers could be prepared selectively in good yields. An efficient three-step route that provides ketone 5 in 75% overall yield was developed.