Highly Enantioselective Catalytic Dynamic Resolution of; N-Boc-2-lithiopiperidine:Synthesisof(R)-(+)-N-Boc-PipecolicAcid,; (S)-(-)-Coniine,(S)-(+)-Pelletierine,(+)beta-Conhydrine,and; (S)-(-)-RopivacaineandFormalSynthesisof(-)-LasubineIIand; (+)-Cermizine
by Beng, Timothy Kum; Gawley, Robert E.
The catalytic dynamic resolution (CDR) of rac-2-lithio-N-Boc-piperidine; usingchiralligand8oritsdiastereomer9inthepresenceofTMEDA; hasledtothehighlyenantioselectivesynthesesofbothenantiomersof; 2-substitutedpiperidinesusingawiderangeofelectrophiles.TheCDR; hasbeenappliedtothesynthesisof(R)-and(S)-pipecolicacid; derivatives,(+)-beta-conhydrine,(S)-(+)-pelletierine,and; (S)-(-)-ropivacaineandtheformalsynthesisof(-)-lasubineIIand; (+)-cermizineC.
- Journal
- Journal of the American Chemical Society
- Volume
- 132
- Issue
- 35
- Year
- 2010
- Start Page
- 12216
- ISBN/ISSN
- 1520-5126; 0002-7863
- PMID
- 20806976
- DOI
- 10.1021/ja105772z