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Literature DB >> 22594458

N-heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles.

Limin Yang¹, Fei Wang, Pei Juan Chua, Yunbo Lv, Liang-Jun Zhong, Guofu Zhong.

Abstract

A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and α-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).

Entities: Chemical Disease

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Year: 2012 PMID： 22594458 DOI： 10.1021/ol301175z

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

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Cited

9 in total

1. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors: Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal: Chem Sci Date: 2014-05-01 Impact factor: 9.825

2. Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application.

Authors: Daniel T Cohen; Ryne C Johnston; Nicholas T Rosson; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-14 Impact factor: 6.222

N-heterocyclic carbene (NHC)-catalyzed highly diastereo- and enantioselective oxo-Diels-Alder reactions for synthesis of fused pyrano[2,3-b]indoles.

1. Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

2. Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application.

3. N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

4. S_NAr-Derived Decomposition By-products Involving Pentafluorophenyl Triazolium Carbenes.

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

6. Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes.

7. NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

8. A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.

9. Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.