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A Novel Asymmetric Synthesis of 3‐(1 H ‐Pyrrol‐1‐yl)‐Substituted β ‐Lactams via a Bismuth Nitrate‐Catalyzed Reaction
Author(s) -
Shaikh Aarif L.,
Banik Bimal K.
Publication year - 2012
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.201100202
Subject(s) - chemistry , diastereomer , enantioselective synthesis , catalysis , pyrrole , ring (chemistry) , stereochemistry , residue (chemistry) , lactam , combinatorial chemistry , proline , optically active , medicinal chemistry , organic chemistry , amino acid , biochemistry
The reaction of racemic α ‐keto β ‐lactams 5a – 5c with the commercially available chiral compound trans ‐4‐hydroxy‐ L ‐proline ( 6 ) in the presence of a catalytic amount of Bi(NO 3 ) 3 ⋅5 H 2 O in EtOH gave a diastereoisomer mixture of β ‐lactams with a pyrrole ring at C(3) ( 7 to 12 ). This is the first enantioselective synthesis of optically active β ‐lactams (=azetidin‐2‐ones) that possess a pyrrolyl residue at C(3), in a single step.
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