✦ LIBER ✦
An Efficient Synthesis of Optically Active trans-(3R,4R)-3-Acetoxy-4-aryl-1-(chrysen-6-yl)azetidin-2-ones Using (+)-Car-3-ene as a Chiral Auxiliary
✍ Scribed by Aarif L. Shaikh; Orlando Esparza; Bimal K. Banik
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- German
- Weight
- 176 KB
- Volume
- 94
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
An efficient enantioselective synthesis of 3‐acetoxy trans‐β‐lactams 7a and 7b via [2+2] cycloaddition reactions of imines 4a and 4b, derived from a polycyclic aromatic amine and bicyclic chiral acid obtained from (+)‐car‐3‐ene, is described. The cycloaddition was found to be highly enantioselective, producing only trans‐(3__R__,4__R__)‐N‐azetidin‐2‐one in very good yields. This is the first report of the synthesis of enantiomerically pure trans‐β‐lactams 7a and 7b with a polycyclic aromatic substituent at N(1) of the azetidin ring.