Phosphine-Catalyzed Enantioselective Dearomative [3+2]-Cycloaddition of 3-Nitroindoles and 2-Nitrobenzofurans.
Angew Chem Int Ed Engl, 2019/04/08;58(16):5422-5426.
Wang H[1], Zhang J[1], Tu Y[2], Zhang J[1, 3]
Affiliations
PMID: 30860302DOI: 10.1002/anie.201900036
Impact factor: 16.823
Abstract
Over the past years, the metal-catalyzed dearomative cycloaddition of 3-nitroindoles and 2-nitrobenzofurans have emerged as a powerful protocol to construct chiral fused heterocyclic rings. However, organocatalytic dearomative reaction of these two classes of heteroarenes has become a long-standing challenging task. Herein, we report the first example of phosphine-catalyzed asymmetric dearomative [3+2]-cycloadditio of 3-nitroindoles and 2-nitrobenzofurans, which provide a new, facile, and efficient protocol for the synthesis of chiral 2,3-fused cyclopentannulated indolines and dihydrobenzofurans by reacting with allenoates and MBH carbonates, respectively through a dearomative [3+2]-cycloaddition.
Keywords: CADA; cycloaddition; dearomatization; nitro-heteroarenes; phosphine catalysis
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