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

• Published in: Tetrahedron letters Vol. 45; no. 32; pp. 6097 - 6100
• Main Authors: Liu, Yi-Tsung, Wong, Jesse K., Tao, Meng, Osterman, Rebecca, Sannigrahi, Mousumi, Girijavallabhan, Viyyoor M., Saksena, Anil
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 02.08.2004; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Sodium triacetoxyborohydride; Stereoselective reduction; Tetrahydropyran and tetrahydrofuran proline; Sodium triacetoxyborohydride; Stereoselective reduction; Tetrahydropyran and tetrahydrofuran proline; tetrahydropyran and tetrahydrofuran proline; stereoselective reduction; sodium triacetoxyborohydride

Graphic 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...