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 |
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Authors: | Aarif L Shaikh Orlando Esparza Bimal K Banik |
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Institution: | The University of Texas Pan American, Department of Chemistry, 1201 West University Drive, Edinburg, Texas 78539, USA |
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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‐(3R,4R)‐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. |
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Keywords: | Enantioselective syntheses Cycloadditions (+)‐Car‐3‐ene |
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