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Literature DB >> 18802520

Dynamic resolution of N-Boc-2-lithiopiperidine.

Iain Coldham¹, Sophie Raimbault, Praful T Chovatia, Jignesh J Patel, Daniele Leonori, Nadeem S Sheikh, David T E Whittaker.

Abstract

Dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine is possible using a chiral ligand; the two enantiomers of this organolithium can be resolved with selectivities of up to 85 : 15 from a selection of 26 chiral diamino-alkoxide ligands screened.

Entities: Chemical

Year: 2008 PMID： 18802520 DOI： 10.1039/b810988e

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

6 in total

1. CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

Authors: Timothy K Beng; Robert E Gawley
Journal: Heterocycles Date: 2012-01-01 Impact factor: 0.831

2. 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 (+)-cermizine C.

Authors: Timothy K Beng; Robert E Gawley
Journal: J Am Chem Soc Date: 2010-09-08 Impact factor: 15.419

3. Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines.

Authors: Timothy K Beng; Jin Sun Woo; Robert E Gawley
Journal: J Am Chem Soc Date: 2012-08-27 Impact factor: 15.419

Dynamic resolution of N-Boc-2-lithiopiperidine.

1. CATALYTIC DYNAMIC RESOLUTION APPLIED TO THE SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES: PREPARATION OF (+)-LUPETIDINE AND (-)-EPIDIHYDROPINIDINE.

2. 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 (+)-cermizine C.

3. Synthetic applications and inversion dynamics of configurationally stable 2-lithio-2-arylpyrrolidines and -piperidines.

4. Dynamics of catalytic resolution of 2-lithio-N-Boc-piperidine by ligand exchange.

5. The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA.

6. Synthesis and kinetic resolution of substituted tetrahydroquinolines by lithiation then electrophilic quench.