Literature DB >> 20462193

Asymmetric deprotonation of N-boc piperidine: react IR monitoring and mechanistic aspects.

Darren Stead1, Giorgio Carbone, Peter O'Brien, Kevin R Campos, Iain Coldham, Adam Sanderson.   

Abstract

The high yielding asymmetric deprotonation trapping of N-Boc piperidine is successfully realized using s-BuLi and a (+)-sparteine surrogate. Monitoring of the lithiation by in situ React IR allowed the direct observation of a prelithiation complex.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20462193     DOI： 10.1021/ja102043e

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


  17 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.  Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates.

Authors:  Timothy K Beng; Hironori Takeuchi; Manuel Weber; Richmond Sarpong
Journal:  Chem Commun (Camb)       Date:  2015-05-04       Impact factor: 6.222

3.  Enantioselective Synthesis of α-(Hetero)aryl Piperidines through Asymmetric Hydrogenation of Pyridinium Salts and Its Mechanistic Insights.

Authors:  Bo Qu; Hari P R Mangunuru; Sergei Tcyrulnikov; Daniel Rivalti; Olga V Zatolochnaya; Dmitry Kurouski; Suttipol Radomkit; Soumik Biswas; Shuklendu Karyakarte; Keith R Fandrick; Joshua D Sieber; Sonia Rodriguez; Jean-Nicolas Desrosiers; Nizar Haddad; Keith McKellop; Scott Pennino; Heewon Lee; Nathan K Yee; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2018-02-20       Impact factor: 6.005

4.  Application of catalytic dynamic resolution of N-Boc-2-lithiopiperidine to the asymmetric synthesis of 2-aryl and 2-vinyl piperidines.

Authors:  Timothy K Beng; Robert E Gawley
Journal:  Org Lett       Date:  2010-12-21       Impact factor: 6.005

5.  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

6.  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

7.  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

8.  A strategy for complex dimer formation when biomimicry fails: total synthesis of ten coccinellid alkaloids.

Authors:  Trevor C Sherwood; Adam H Trotta; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2014-06-24       Impact factor: 15.419

9.  Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species.

Authors:  Alexander P Pulis; Ana Varela; Cinzia Citti; Pradip Songara; Daniele Leonori; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-07       Impact factor: 15.336

Review 10.  Opportunities and challenges for direct C-H functionalization of piperazines.

Authors:  Zhishi Ye; Kristen E Gettys; Mingji Dai
Journal:  Beilstein J Org Chem       Date:  2016-04-13       Impact factor: 2.883
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.