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

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...

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Published inTetrahedron 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
LanguageEnglish
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
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Summary: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 the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.06.070