1-(Dialkylaminomethyl)-azetidin-2-ones. Intermediates in a highly stereoselective preparation of trans-3,4-disubstituted azetidin-2-ones | Zendy

A. B. HAMLET | Zendy; Tony Durst | Zendy

Open Access

1-(Dialkylaminomethyl)-azetidin-2-ones. Intermediates in a highly stereoselective preparation of trans-3,4-disubstituted azetidin-2-ones

Author(s) -

A. B. HAMLET,

Tony Durst

Publication year - 1983

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v83-073

Subject(s) - chemistry , thienamycin , stereoselectivity , substituent , electrophile , yield (engineering) , reagent , combinatorial chemistry , aqueous solution , organic chemistry , catalysis , antibiotics , biochemistry , materials science , metallurgy

The use of dialkylaminomethyl derivatives as a new β-lactam N—H protecting group is described. The group is stable to basic reagents but is readily removed with dilute aqueous acids. 1-Dialkylaminomethyl derivatives bearing a 4-substituent are converted in good yield and with high stereoselectivity into trans-3,4-disubstituted derivatives via reaction with LDA and subsequent addition of electrophiles. The products of several of these sequences are of interest as intermediates to thienamycin related substances.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research