Stereoselective synthesis of enantiopure 4,5-disubstituted pyrrolidin-2-ones by consecutive cuprate addition and N-acyliminium coupling

DOI: 10.1016/S0040-4039(00)74791-5

Source and publish data:

Tetrahedron Letters p. 7969 - 7972 (1992)

Update date:2022-08-03

Topics:

Authors:

Koot, Wim-Jan

Hiemstra, Henk

Speckamp, W. Nico

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Article abstract of DOI:10.1016/S0040-4039(00)74791-5

The enantiopure γ-lactam (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one (1), prepared from (S)-malic acid, undergoes cuprate addition at C4 with complete trans-stereoselectivity. The products react with π-nucleophiles in the presence of Lewis acid at C5 to provide enantiopure, 4,5-disubstituted pyrrolidin-2-ones.

Full text of DOI:10.1016/S0040-4039(00)74791-5

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Product name:(4S,5R)-1-Acetyl-5-isopropoxy-4-phenethyl-pyrrolidin-2-one

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