Literature DB >> 19707632

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

Iain Coldham1, Daniele Leonori, Timothy K Beng, Robert E Gawley.   

Abstract

The kinetics of enantiomerization and dynamic thermodynamic resolution (DTR) of N-Boc-2-lithiopiperidine have been measured, revealing significant differences in enthalpy and entropy for these processes and a role for the achiral ligand TMEDA; the racemization and the DTR are catalytic and first order in [TMEDA], and this has implications for asymmetric synthesis with chiral organolithiums.

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Year:  2009        PMID： 19707632      PMCID： PMC2764334          DOI： 10.1039/b911024k

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


  19 in total

1.  Dynamic thermodynamic resolution: control of enantioselectivity through diastereomeric equilibration.

Authors:  P Beak; D R Anderson; M D Curtis; J M Laumer; D J Pippel; G A Weisenburger
Journal:  Acc Chem Res       Date:  2000-10       Impact factor: 22.384

2.  Asymmetric syntheses of fused bicyclic lactams.

Authors:  S H Lim; S Ma; P Beak
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

3.  Reactivity series for s-BuLi/diamine-mediated lithiation of N-Boc pyrrolidine: applications in catalysis and lithiation of N-Boc piperidine.

Authors:  Matthew J McGrath; Julia L Bilke; Peter O'Brien
Journal:  Chem Commun (Camb)       Date:  2006-05-10       Impact factor: 6.222

4.  Dynamic thermodynamic resolution: advantage by separation of equilibration and resolution.

Authors:  Won Koo Lee; Yong Sun Park; Peter Beak
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

5.  Dynamic resolution of N-Boc-2-lithiopiperidine.

Authors:  Iain Coldham; Sophie Raimbault; Praful T Chovatia; Jignesh J Patel; Daniele Leonori; Nadeem S Sheikh; David T E Whittaker
Journal:  Chem Commun (Camb)       Date:  2008-08-08       Impact factor: 6.222

6.  Reaction of alpha-(N-carbamoyl)alkylcuprates with propargyl substrates: synthetic route to alpha-amino allenes and delta3-pyrrolines.

Authors:  R Karl Dieter; Ningyi Chen; Huayun Yu; Lois E Nice; Vinayak K Gore
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

7.  Solution structures and reactivities of the mixed aggregates derived from n-butyllithium and vicinal amino alkoxides.

Authors:  X Sun; M D Winemiller; B Xiang; D B Collum
Journal:  J Am Chem Soc       Date:  2001-08-22       Impact factor: 15.419

8.  A theoretical study on nBuLi/lithium aminoalkoxide aggregation in hexane and THF.

Authors:  Hassan K Khartabil; Philippe C Gros; Yves Fort; Manuel F Ruiz-López
Journal:  J Org Chem       Date:  2008-12-05       Impact factor: 4.354

9.  Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine.

Authors:  Timothy K Beng; Taher I Yousaf; Iain Coldham; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2009-05-27       Impact factor: 15.419

10.  NMR studies of structure and reorganization dynamics of an [6Li]-allylic lithium compound complexed to [14N,15N]-N,N,N',N'-tetramethylethylenediamine: inversion and ligand lithium exchange.

Authors:  Gideon Fraenkel; Hua Liu
Journal:  J Am Chem Soc       Date:  2004-04-28       Impact factor: 15.419
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  1 in total

1.  Fully substituted carbon centers by diastereoselective spirocyclization: stereoselective synthesis of (+)-lepadiformine C.

Authors:  Matthew A Perry; Matthew D Morin; Brian W Slafer; Scott A Wolckenhauer; Scott D Rychnovsky
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419
  1 in total

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