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

Full Text: HTML

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 ...

Related Articles:

Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst …

[Sattely, Elizabeth S.; Alexander Cortez; Moebius, David C.; Schrock, Richard R.; Hoveyda, Amir H. Journal of the American Chemical Society, 2005 , vol. 127, # 23 p. 8526 - 8533]

Conversion of N-acyl-2, 3-dihydro-4-pyridones to 4-chloro-1, 2-dihydropyridines using the Vilsmeier Reagent. Synthesis of (-)-coniine and (±)-lupinine

[Al-awar, Rima S.; Joseph, Sajan P.; Comins, Daniel L. Journal of Organic Chemistry, 1993 , vol. 58, # 27 p. 7732 - 7739]

Intramolecular hydroamination/cyclization of conjugated aminodienes catalyzed by organolanthanide complexes. Scope, diastereo-and enantioselectivity, and …

[Hong, Sukwon; Kawaoka, Amber M.; Marks, Tobin J. Journal of the American Chemical Society, 2003 , vol. 125, # 51 p. 15878 - 15892]

Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst …

[Sattely, Elizabeth S.; Alexander Cortez; Moebius, David C.; Schrock, Richard R.; Hoveyda, Amir H. Journal of the American Chemical Society, 2005 , vol. 127, # 23 p. 8526 - 8533]

Design and stereoselective preparation of a new class of chiral olefin metathesis catalysts and application to enantioselective synthesis of quebrachamine: catalyst …

[Sattely, Elizabeth S.; Alexander Cortez; Moebius, David C.; Schrock, Richard R.; Hoveyda, Amir H. Journal of the American Chemical Society, 2005 , vol. 127, # 23 p. 8526 - 8533]

More Articles...