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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 6
BKCSDE 22(6)
June 20, 2001 

A Stereoselective Synthesis of 1 β-Aminocarbapenems
Kyung Jae Seo, Tae Ho Lee, Youn Young Lee
Carbapenems, Phosphite-mediated reductive cyclization, Benzophenone imines of glycine esters.
A stereoselective synthesis of 1 β-aminocarbapenems (11a-c) starting from 4-acetoxy-2-azetidinone derivative 4 is described. 4-Acetoxy-2-azetidinone derivative (4) was reacted with the lithium enolate of benzophenone imine of glycine phenyl ester (5f) to give alkylated product (R)-6f in good yield with high diastereoselectivity. The alkylated product (R)-6f was transformed to thioesters (7a-c) by transesterification with thiols, Thioesters (7a-c) were converted to their oxalimides (8a-c), followed by the phosphite-mediated reductive cyclization to give carbapenems (9a-c). Removal of all protecting groups of carbapenems (9a-c) afforded 1 β-aminocarbapenems (11a-c).
553 - 558
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