Diastereoselective synthesis of <i>trans</i>-2,3-dihydroindoles <i>via</i> formal [4 + 1] annulation reactions of a sulfonium ylide

Jain, Anshul; Kumari, Akanksha; Metre, Ramesh K.; Rana, Nirmal K.

doi:10.1039/d3ob01793a

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01793a

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Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide

Anshul Jain,

Akanksha Kumari,

Ramesh K. Metre

et al.

Abstract: We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disunstituted-2,3-dihydoindoles. The [4+1] annulation approach relied on Michael addition/substitution reactions. These reactions are carried out at ambient temperature...

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Cited by 2 publications

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Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Sun,

Ling,

Chen

2024

Asian J Org Chem

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Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Sun,

Ling,

Chen

2024

Asian J Org Chem

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Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide

Saha,

Bera,

Kumari

et al. 2024

J. Org. Chem.

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We report a cascade approach for the synthesis of 2,3-dihydropyrroles derivatives via a formal [4 + 1] annulation reaction of α,β-unsaturated imines with in situ generated pyridinium ylides. Importantly, this protocol is compatible with diverse substituted imines as well as pyridinium ylides, constructing 2,3-dihydropyrroles with excellent yield and selectivity. Thereafter, the Merrifield resin-supported pyridinium ylide as a potential C1 synthon was also employed in our strategy and reused several times, resulting in products with excellent yield and diastereoselectivity.

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Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide

Abstract: We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disunstituted-2,3-dihydoindoles. The [4+1] annulation approach relied on Michael addition/substitution reactions. These reactions are carried out at ambient temperature...

Cited by 2 publications

References 38 publications

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide

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Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4 + 1] annulation reactions of a sulfonium ylide

Abstract: We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disunstituted-2,3-dihydoindoles. The [4+1] annulation approach relied on Michael addition/substitution reactions. These reactions are carried out at ambient temperature...

Cited by 2 publications

References 38 publications

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF3−Imidoyl Sulfoxonium Ylides

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF3−Imidoyl Sulfoxonium Ylides

Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4 + 1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide

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Product

Resources

About

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides