Tetrahedron p. 3719 - 3740 (1996)
Update date:2022-08-04
Topics:
Beard, Mark J.
Bailey, Jonathan H.
Cherry, David T.
Moloney, Mark G.
Shim, Sung Bo
Statham, Kathryn A.
Bamford, Mark J.
Lamont, R. Brian
The generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.
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Doi:10.1021/ja953686h
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(2014)
