Literature DB >> 19405472

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

Timothy K Beng1, Taher I Yousaf, Iain Coldham, Robert E Gawley.   

Abstract

The barriers to enantiomerization of N-trimethylallyl-2-lithiopyrrolidine have been measured in the presence of sparteine,1, N,N'-diisopropylbispidine, 2, and diaminoalkoxide 3. We have additionally demonstrated a rare example of a catalytic dynamic resolution using either of two ligands, achieving enantiomer ratios of up to 93:7.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19405472      PMCID： PMC2768471          DOI： 10.1021/ja900755a

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 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.  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

3.  Catalytic asymmetric deprotonation using a ligand exchange approach.

Authors:  Matthew J McGrath; Peter O'Brien
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

4.  Dynamic thermodynamic and dynamic kinetic resolution of 2-lithiopyrrolidines.

Authors:  Iain Coldham; Samuel Dufour; Thomas F N Haxell; Jignesh J Patel; Graciela Sanchez-Jimenez
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

5.  Dynamic kinetic resolution of N-Boc-2-lithiopyrrolidine.

Authors:  Iain Coldham; Jignesh J Patel; Graciela Sanchez-Jimenez
Journal:  Chem Commun (Camb)       Date:  2005-05-11       Impact factor: 6.222

6.  Barrier to enantiomerization of unstabilized, chelated, and dipole-stabilized 2-lithiopyrrolidines.

Authors:  Neil J Ashweek; Peter Brandt; Iain Coldham; Samuel Dufour; Robert E Gawley; Fredrik Haeffner; Rosalyn Klein; Graciela Sanchez-Jimenez
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

7.  Highly enantioselective reactions of alpha-sulfonyl carbanions of trifluoromethyl sulfones.

Authors:  Shuichi Nakamura; Norimune Hirata; Takeshi Kita; Ryusuke Yamada; Daisuke Nakane; Norio Shibata; Takeshi Toru
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Catalytic and highly enantioselective reactions of alpha-sulfonyl carbanions with chiral bis(oxazoline)s.

Authors:  Shuichi Nakamura; Norimune Hirata; Ryusuke Yamada; Takeshi Kita; Norio Shibata; Takeshi Toru
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

9.  The barrier to enantiomerization of N-Boc-2-lithiopyrrolidine: the effect of chiral and achiral diamines.

Authors:  Taher I Yousaf; Roger L Williams; Iain Coldham; Robert E Gawley
Journal:  Chem Commun (Camb)       Date:  2008-01-07       Impact factor: 6.222
  9 in total
  7 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Overview of Carbanion Dynamics and Electrophilic Substitutions in Chiral Organolithium Compounds.

Authors:  Robert E Gawley
Journal:  Top Stereochem       Date:  2010-01-01

3.  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

4.  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

5.  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

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

Authors:  Timothy K Beng; William S Tyree; Trent Parker; Chicheung Su; Paul G Williard; Robert E Gawley
Journal:  J Am Chem Soc       Date:  2012-09-25       Impact factor: 15.419

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

Authors:  Iain Coldham; Daniele Leonori; Timothy K Beng; Robert E Gawley
Journal:  Chem Commun (Camb)       Date:  2009-08-06       Impact factor: 6.222
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.