Abstract
The Strecker reaction of (2R,4R)-2-phenyl-3-phenoxycarbonylthiazolidine-4-carbaldehyde (4b), which was readily prepared from l-cysteine, with benzylamine and trimethylsilyl cyanide provided α-amino nitrile 5b stereoselectively (syn-anti, 2:1). Amidation of 5b and subsequent cyclization gave bicyclic compound 6, which, upon reduction with zinc dust, hydrolysis and subsequent cyclization, furnished thiolactone 2, a key intermediate for (+)-biotin (1).
Keywords
amino acids - amino aldehydes - ring closure - stereoselectivity - vitamins - biotin - Strecker reaction
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[6]
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[5]
Although the approach can provide 2 in 9 steps, it requires expensive or hazardous reagents such as BnNCO and CDI.
