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

作者：Shaikh Aarif L; Esparza Orlando; Banik Bimal K^*

来源：Helvetica Chimica Acta, 2011, 94(12): 2188-2193.

DOI：10.1002/hlca.201100225

• Enantioselective syntheses
• Cycloadditions
• (+)-Car-3-ene

An efficient enantioselective synthesis of 3-acetoxy trans-beta-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-beta-lactams 7a and 7b with a polycyclic aromatic substituent at N(1) of the azetidin ring.

• 出版日期2011-12