Synthesis of β-lactams by condensation of the tin enolates of 2-pyridylthioesters with imines. A comparison between titanium and tin enolates

DOI: 10.1016/S0040-4020(01)85649-0

Source and publish data:

Tetrahedron p. 5821 - 5828 (1994)

Update date:2022-09-26

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Authors:

Annunziata, Rita

Benaglia, Maurizio

Cinquini, Mauro

Cozzi, Franco

Raimondi, Laura

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Article abstract of DOI:10.1016/S0040-4020(01)85649-0

Addition of triethylamine to a mixture of 2-pyridylthioesters and SnCl₄ or SnBr₄ affords the corresponding tin(IV) enolates that add to imines to give β-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl₄ and TiBr₄.

Full text of DOI:10.1016/S0040-4020(01)85649-0

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