A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine.
The s-BuLi complex of a cyclohexane-derived diamine is as efficient as s-BuLi/(-)-sparteine for the asymmetric deprotonation of N-Boc pyrrolidine. This is the first example of high enantioselectivity using a non-sparteine-like diamine in such reactions. The (S,S)-diamine is a useful (+)-sparteine surrogate and was utilized in short syntheses of (-)-indolizidine 167B and an intermediate for the synthesis of the CCK antagonist (+)-RP 66803.
Stead
Darren
D
Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom.
O'Brien
Peter
P
Sanderson
Adam
A
D002766:Cholecystokinin / Q000037:antagonists & inhibitors; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D011759:Pyrrolidines / Q000737:chemistry*; D013034:Sparteine / Q000737:chemistry*; D013237:Stereoisomerism
C413205:167B indolizidine; D003959:Diamines; D007212:Indolizines; D011759:Pyrrolidines; C499756:RP 66803; D013034:Sparteine; D002766:Cholecystokinin; D011392:Proline