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A novel, general, totally stereoselective one-pot synthesis of cis-3-substituted 4-formylazetidin-2-ones

✍ Scribed by Benito Alcaide; Yolanda Martín-Cantalejo; Joaquín Plumet; Julián Rodríguez-López; Miguel A. Sierra

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
275 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general , totally stereoselectrve one-pot synthesis of cls-3-substttuted-+formylazetrdtn-2-ones based upon the reacuon of actd chlorides and 1,4-b~s-(4-methoxyphenyl)-I,4-drazabuta-IJ-d~ene, as synthettc equrvalent of the correspondmg unknown a-formyhmtne, has been developed

Appropnately as-substituted 4-formylazetuhn-2-one denvanves are versatile butidmg blocks' for the qynthesrs of blologtcally acnve plactam antibiotics,2 mcludmg ~rar~-and as-carbapenems,3 monobactams and lsocepham antlblotlcs 4 Routes to such valuable mtermehates have hitherto involved either oxldatlve degradatron or multlstep functional group transformanon from appropnate 4-subsmuted p-lactams (le, 4styryi -,WcJeS, 4-OXIIZ$-, lfor 4-alkoxycarbonyl-P-lactamsla6)

The use of 1,4-dlaza-1,3aenes (a-dmnmes) m synthesis of 4-formylazetldm-2-ones by reaction with

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