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A regioselective reductive cleavage of benzylidene acetal: stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid

✍ Scribed by Ponminor Senthil Kumar; Sundarababu Baskaran


Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
341 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis


A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from D-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14.