Functionalised pyrrolidinones derived from (S)-pyroglutamic acid
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.
Beard, Mark J.,Bailey, Jonathan H.,Cherry, David T.,Moloney, Mark G.,Shim, Sung Bo,Statham, Kathryn A.,Bamford, Mark J.,Lamont, R. Brian
p. 3719 - 3740
(2007/10/03)
A CONSISE APPROACH TO FUNCTIONALISED, HOMOCHIRAL PYRROLIDINONES
Acylation of O,N-acetal 1 gives excellent yields of the C-7 substituted products 2a,b.Alkylation of 2a under mild conditions gives high yields of the exo- 3 and endo- 4 substituted products in varying ratios, depending on the alkylating agent.The unsatura
Bamford, Mark J.,Beard, Mark,Cherry, David T.,Moloney, Mark G.
p. 337 - 340
(2007/10/02)
Stereoselective methylations of bicyclic lactams derived from pyroglutamic acid
Reaction of the lithium enolate of (-)7 with iodomethane provides a stereoselective synthesis of (2R,4S)-4-amino-2-methylpentanamide derivatives.
Armstrong,DeMattei
p. 5749 - 5752
(2007/10/02)
(L)-pyroglutamic acid as a chiral starting material for asymmetric synthesis
Elaboration of lactam (1), readily available from (L)-pyroglutamic acid, provides access to a range of 2,4- and 2,3,4-substituted pyrrolidinones.
Baldwin, Jack E.,Moloney, Mark G.,Shim, Sung Bo
p. 1379 - 1380
(2007/10/02)
More Articles about upstream products of 138231-09-1