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