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An Efficient Synthesis of Optically Active trans ‐(3 R ,4 R )‐3‐Acetoxy‐4‐aryl‐1‐(chrysen‐6‐yl)azetidin‐2‐ones Using (+)‐Car‐3‐ene as a Chiral Auxiliary
Author(s) -
Shaikh Aarif L.,
Esparza Orlando,
Banik Bimal K.
Publication year - 2011
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100225
Subject(s) - chemistry , enantioselective synthesis , cycloaddition , substituent , amine gas treating , aryl , ring (chemistry) , bicyclic molecule , stereochemistry , ene reaction , medicinal chemistry , catalysis , organic chemistry , alkyl
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.