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ChemInform Abstract: A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams.

✍ Scribed by Tetsuo Iwama; Tadashi Kataoka; Osamu Muraoka; Genzoh Tanabe

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199915039

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✦ Synopsis

A New Synthesis of α-Amino Acid Thioesters by Pummerer Reaction of 3-Substituted-4-sulfinyl-β-sultams.

-trans-Sultams (I), (V), and (VII), obtained in all cases as two separable epimers at the sulfoxide group, are each converted to the title thioesters via sulfenylation and Pummerer rearrangement with high or complete retention of configuration. A preliminary study on diastereoselective synthesis of β-sultams in solution phase is also presented.

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