61612-37-1Relevant articles and documents
Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: Synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines
Liu, Yi-Tsung,Wong, Jesse K.,Tao, Meng,Osterman, Rebecca,Sannigrahi, Mousumi,Girijavallabhan, Viyyoor M.,Saksena, Anil
, p. 6097 - 6100 (2007/10/03)
In the presence of a carboxyl group positioned for participation, NaBH(OAc)3 will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2. These results are consistent with the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride.