Highly Enantioselective Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine: Synthesis of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)beta-Conhydrine, and (S)-(-)-Ropivacaine and Formal Synthesis of (-)-Lasubine II and (+)
by Beng, T. K.; Gawley, R. E.
The catalytic dynamic resolution (CDR) of rac-2-lithio-N-Boc-piperidine using chiral ligand 8 or its diastereomer 9 in the presence of TMEDA has led to the highly enantioselective syntheses of both enantiomers of 2-substituted piperidines using a wide range of electrophiles. The CDR has been applied to the synthesis of (R)- and (S)-pipecolic acid derivatives, (+)-beta-conhydrine, (S)-(+)-pelletierine, and (S)-(-)-ropivacaine and the formal synthesis of (-)-lasubine II and (+)-cermizine C.
- Journal
- Journal of the American Chemical Society
- Volume
- 132
- Issue
- 35
- Year
- 2010
- Start Page
- 12216-12217
- URL
- https://dx.doi.org/10.1021/ja105772z
- ISBN/ISSN
- 1520-5126; 0002-7863
- DOI
- 10.1021/ja105772z