Journal of the Chemical Society, Perkin Transactions 1

Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of (▒)-thienamycin

JD Kilburn

Index: Fleming, Ian; Kilburn, Jeremy D. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2663 - 2671

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Abstract

The lithium enolate-11 derived from methyl 3-dimethyl (phenyl) silylbutanoate reacts with the- silylimines of cinnamaldehyde 12, of 3-trimethylsilylpropynal 18, and of 3- trimethylsilylpropenal 19 to give β-lactams with a high level of stereoselection in favour of the isomers 13, 20 and 21, respectively. The dimethy