Abstract
Treatment of serine-derived N-(alpha-haloacetamido)dehydroalanine derivatives with tributyltin hydride in boiling benzene or toluene afforded pyroglutamates in 47-84% yield. The radical cyclisation reaction, which proceeded regioselectively in a disfavoured 5-endo-trig manner, was found to be most efficient when dichloro- and trichloroamides were employed as starting materials. Copyright (C) 1996 Elsevier Science Ltd
Original language | English |
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Pages (from-to) | 6739-6758 |
Number of pages | 20 |
Journal | Tetrahedron |
Volume | 52 |
Issue number | 19 |
Publication status | Published - 6 May 1996 |
Keywords
- CHIRAL STARTING MATERIAL
- N-ALLYLTRICHLOROACETAMIDES
- CHIROSPECIFIC SYNTHESES
- (L)-PYROGLUTAMIC ACID
- GLUTAMIC-ACID
- GAMMA-LACTAMS
- AMINO-ACIDS
- ACETIC-ACID
- CYCLIZATION
- 5-ENDO-TRIG