Premium
Oxazoline N ‐Oxide Mediated [3+2] Cycloadditions: Application to a Formal Synthesis of a (+)‐β‐Methylcarbapenem
Author(s) -
Mauduit Marc,
Kouklovsky Cyrille,
Langlois Yves
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200004)2000:8<1595::aid-ejoc1595>3.0.co;2-e
Subject(s) - chemistry , cycloaddition , oxazoline , stereoselectivity , derivative (finance) , adduct , formal synthesis , hydrolysis , stereochemistry , side chain , medicinal chemistry , organic chemistry , catalysis , polymer , financial economics , economics
[3+2] Cycloaddition between a camphor‐derived oxazoline N ‐oxide 9 and the γ,δ‐unsaturated enamino ester 11 afforded the single adduct 6 . A stereoselective reduction of the enamino ester side chain allowed the control of the absolute configuration of the two additional asymmetric centres. Nitrogen protection and oxidative hydrolysis of the resulting product 13 , followed by further functional group manipulations, led to the β‐lactam derivative 1 , a known precursor of the β‐methylthienamycin derivative 2a .