Highly Enantioselective Catalytic Dynamic Resolution of N -Boc-2-lithiopiperidine: Synthesis of ( R )-(+)- N- Boc-Pipecolic Acid, ( S )-(−)-Coniine, ( S )-(+)-Pelletierine, (+)-β-Conhydrine, and ( S )-(−)-Ropivacaine and Formal Synthesis of (−)-Lasubine II and (+)-Cermizine C
Year: 2010
Type: article
Abstract: 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.
DOI: 10.1021/ja105772z
Authors: Timothy K. Beng, Robert E. Gawley
Institution: University of Arkansas at Fayetteville
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2012784905