Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5422-5426Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900036
Keywords
CADA; cycloaddition; dearomatization; nitro-heteroarenes; phosphine catalysis
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Funding
- 973 Programs [2015CB856600]
- National Natural Science Foundation of China [21425205]
- Changjiang Scholars and Innovative Research Team in University (PCSIRT)
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Over the past years, the metal-catalyzed dearomative cycloaddition of 3-nitroindoles and 2-nitrobenzofitrans 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.
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