A convenient method for 3-pyrroline synthesis.
[reaction: see text]. The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and the formation of nitrogen-bearing quaternary stereocenters is a relatively facile process. The insertion reaction occurs with >95% retention of stereochemistry, but the presence of protecting groups on nitrogen is generally deleterious to the cyclization process.
Green
M P
MP
The School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Prodger
J C
JC
Sherlock
A E
AE
Hayes
C J
CJ
D000111:Acetylcysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007769:Lactams; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007769:Lactams; D011758:Pyrroles; C067713:lactacystin; C013231:pyrroline; D000111:Acetylcysteine