ArticleAngewandte Chemie (International ed. in English)2023
Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β-Unsaturated Esters.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Catalytic Enantioselective Intramolecular Aza-Michael Addition to α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2026Article
- Catalytic Enantioselective Dearomatizing [2,3]-Wittig Rearrangements Allow Divergent [2,3]-, [1,2]-, and Sommelet-Hauser-Type Products.Journal of the American Chemical Society · 2026Article
- Enantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.Journal of the American Chemical Society · 2025Article
- Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides.Journal of the American Chemical Society · 2023Article
- Catalytic, Asymmetric Michael-Aldol Annulations via a Stereodivergent/Stereoconvergent Path Operating under Curtin-Hammett Control.Journal of the American Chemical Society · 2023Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Nitroalkane Addition to Unactivated α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
6 authors.
Funding
Abstract
Herein we describe the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated α,β-unsaturated esters, catalyzed by a bifunctional iminophosphorane (BIMP) superbase. The transformation provides the most direct access to pharmaceutically relevant enantioenriched γ-nitroesters, utilizing feedstock chemicals, with unprecedented selectivity. The methodology exhibits a broad substrate scope, including β-(fluoro)alkyl, aryl and heteroaryl substituted electrophiles, and was successfully applied on a gram scale with reduced catalyst loading, and, additionally, catalyst recovery was carried out. The formal synthesis of a range of drug molecules, and an enantioselective synthesis of (S)-rolipram were achieved. Additionally, computational studies revealed key reaction intermediates and transition state structures, and provided rationale for high enantioselectivities, in good agreement with experimental results.
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Registered trials
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