Literature DB >> 23061465

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.

Hui Lv1, Bhoopendra Tiwari, Junming Mo, Chong Xing, Yonggui Robin Chi.   

Abstract

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

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Year:  2012        PMID： 23061465     DOI： 10.1021/ol302475g

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


  9 in total

1.  Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3-Fluorinated and All-Carbon Quaternary Oxindoles.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-27       Impact factor: 15.336

2.  Stereoselective Synthesis of 3,3'-Bisindolines by Organocatalytic Michael Additions of Fluorooxindole Enolates to Isatylidene Malononitriles in Aqueous Solution.

Authors:  Kaluvu Balaraman; Ransheng Ding; Christian Wolf
Journal:  Adv Synth Catal       Date:  2017-09-22       Impact factor: 5.837

3.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

Authors:  Ki Po Jang; Gerri E Hutson; Ryne C Johnston; Elizabeth O McCusker; Paul H-Y Cheong; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

4.  Asymmetric catalytic aza-Morita-Baylis-Hillman reaction for the synthesis of 3-substituted-3-aminooxindoles with chiral quaternary carbon centers.

Authors:  Fang-Le Hu; Yin Wei; Min Shi; Suresh Pindi; Guigen Li
Journal:  Org Biomol Chem       Date:  2013-02-13       Impact factor: 3.876

5.  Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Authors:  Qijian Ni; Xiaoxiao Song; Jiawen Xiong; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

6.  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

7.  Enantioconvergent synthesis of functionalized γ-butyrolactones via (3 + 2)-annulation.

Authors:  C Guy Goodman; Morgan M Walker; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-12-23       Impact factor: 15.419

8.  Construction of Dihydropyrido[2,3-d]pyrimidine Scaffolds via Aza-Claisen Rearrangement Catalyzed by N-Heterocyclic Carbenes.

Authors:  Krzysztof Dzieszkowski; Izabela Barańska; Zbigniew Rafiński
Journal:  J Org Chem       Date:  2020-04-29       Impact factor: 4.354

9.  Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence.

Authors:  Amarendar Reddy Maddirala; Peter R Andreana
Journal:  Beilstein J Org Chem       Date:  2018-04-18       Impact factor: 2.883
  9 in total

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