Literature DB >> 24067098

Organocatalytic enantioselective γ-aminoalkylation of unsaturated ester: access to pipecolic acid derivatives.

Jianfeng Xu1, Zhichao Jin, Yonggui Robin Chi.   

Abstract

The direct γ-carbon functionalization of α,β-unsaturated esters via N-Heterocyclic Carbene (NHC) catalysis is disclosed. This catalytically generated nucleophilic γ-carbon undergoes highly enantioselective additions to hydrazones. The resulting δ-lactam products can be readily transformed to optically enriched pipecolic acid derivatives.

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Year:  2013        PMID： 24067098     DOI： 10.1021/ol402358k

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Enantioselective γ-Alkylation of α,β-Unsaturated Malonates and Ketoesters by a Sequential Ir-Catalyzed Asymmetric Allylic Alkylation/Cope Rearrangement.

Authors:  Wen-Bo Liu; Noriko Okamoto; Eric J Alexy; Allen Y Hong; Kristy Tran; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-04-18       Impact factor: 15.419

2.  N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Chem Commun (Camb)       Date:  2015-02-25       Impact factor: 6.222

3.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

4.  Asymmetric δ-Lactam Synthesis with a Monomeric Streptavidin Artificial Metalloenzyme.

Authors:  Isra S Hassan; Angeline N Ta; Michael W Danneman; Natthawat Semakul; Matthew Burns; Corey H Basch; Vanessa N Dippon; Brian R McNaughton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-03-13       Impact factor: 15.419

5.  Electroredox carbene organocatalysis with iodide as promoter.

Authors:  Peng Zhou; Wenchang Li; Jianyong Lan; Tingshun Zhu
Journal:  Nat Commun       Date:  2022-07-02       Impact factor: 17.694

6.  Direct Regio- and Diastereoselective Synthesis of δ-Lactams from Acrylamides and Unactivated Alkenes Initiated by RhIII -Catalyzed C-H Activation.

Authors:  Sumin Lee; Natthawat Semakul; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-11       Impact factor: 15.336

7.  An Asymmetric Organocatalytic Quadruple Cascade to Tetraaryl-Substituted 2-Azabicyclo[3.3.0]octadienones.

Authors:  Céline Joie; Kristina Deckers; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-06-01       Impact factor: 3.157

8.  NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Authors:  Lei Wang; Qijian Ni; Marcus Blümel; Tao Shu; Gerhard Raabe; Dieter Enders
Journal:  Chemistry       Date:  2015-04-15       Impact factor: 5.236

9.  Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Authors:  Anna Lee; Ashkaan Younai; Christopher K Price; Javier Izquierdo; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2014-07-15       Impact factor: 15.419

10.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
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