Journal of the American Chemical Society

Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: Synthesis of (R)-(+)-N-Boc-pipecolic acid,(S)-(−)-coniine,(S)-(+)-pelletierine,(+)-β- …

TK Beng, RE Gawley

Index: Beng, Timothy K.; Gawley, Robert E. Journal of the American Chemical Society, 2010 , vol. 132, # 35 p. 12216 - 12217

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Citation Number: 2

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,(+)-β-conhydrine,(S)-(+)-pelletierine, and (S)-(−)-ropivacaine and the formal ...