Tetrahedron letters

Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: synthesis of novel 3, 4-fused tetrahydropyran and tetrahydrofuran prolines

YT Liu, JK Wong, M Tao, R Osterman, M Sannigrahi…

Index: Liu, Yi-Tsung; Wong, Jesse K.; Tao, Meng; Osterman, Rebecca; Sannigrahi, Mousumi; Girijavallabhan, Viyyoor M.; Saksena, Anil Tetrahedron Letters, 2004 , vol. 45, # 32 p. 6097 - 6100

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Citation Number: 14

Abstract

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 and toward the title compounds and. 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.

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