Title of article :
An efficient and practical procedure for Strecker reaction: a highly diastereoselective synthesis of a key intermediate for (+)-biotin
Author/Authors :
Seki، نويسنده , , Masahiko and Hatsuda، نويسنده , , Masanori and Yoshida، نويسنده , , Shin-ichi، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2004
Abstract :
Treatment of α-amino aldehyde 2, which was prepared through Moffatt oxidation of the corresponding β-amino alcohol 5, with aqueous sodium bisulfite allowed clean conversion to a water-soluble bisulfite adduct 6 [>99% conversion, 89% yield (two steps)]. The aqueous solution of 6 was treated with benzylamine followed by easy-handling NaCN to effect the Strecker reaction to afford α-amino nitrile 3 with high diastereoselectivity and in high yield (syn/anti = 11:1, 95% assay yield). Both the compounds syn-3 and anti-3 were converted to a key intermediate 4 for (+)-biotin through S,N-carbonyl migration in high yields.
Journal title :
Tetrahedron Letters
Journal title :
Tetrahedron Letters