ChemInform Abstract: An Efficient β‐Amino Acid Cyclodehydration Using Methanesulfonyl Chloride to Thienamycin Intermediate 3‐(1‐Hydroxyethyl)‐4‐( methoxycarbonylmethyl)azetidin‐2‐one.

Abstract

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SmI2-promoted imino-Reformatsky reaction for facile synthesis of enantioenriched β-amino acid esters

“…As illustrated in Scheme 1, removal of the sulfinyl group and tert-butyl ester under acidic conditions, followed by cyclization using the literature procedure [32], afforded the corresponding -lactam 4c in good yield. The chirl HPLC analysis of 4c clearly revealed its excellent enantiomeric excess (95% ee), and the major enantiomer is speculated to has S configuration by comparison to literature optical rotation value [25].…”

“…Both of these compounds are valuable intermediates and exhibit interesting biological activities [34,35]. With the obtained -amino acid esters, the sulfinyl group and tert-butyl ester can be easily cleaved by acidic hydrolysis in one step to give free -amino acids in high yields, which then undergo further lactamization [32] or Friedel-Crafts acylation [36] conveniently to furnish the corresponding -lactams (4) and 3-aminoindan-1-ones (6) without loss of enantioselectivity (Scheme 3).…”