Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 32, Pages 10373-10377Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806372
Keywords
asymmetric catalysis; heterocycles; hydroarylation; ligand design; palladium
Categories
Funding
- NSFC [21425205, 21672067]
- 973 Program [2015CB856600]
- China Postdoctoral Science Foundation [2017M610236, 2018T110369]
- Program of Eastern Scholar at Shanghai Institutions of Higher Learning
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The first example of highly enantioselective intramolecular hydroarylation of allyl aryl ethers was realized by palladium-catalyzed reductive heck reactions utilizing a new chiral sulfinamide phosphine ligand (N-Me-XuPhos). N-Me-XuPhos can be easily prepared on gram scale from readily available starting materials in a one-pot synthesis approach. A series of optically active 2,3-dihydrobenzofurans bearing a quaternary stereocenter were obtained in good yields and with excellent enantioselectivities. The practicality of this reaction was validated in the straightforward synthesis of CB2 receptor agonists. Moreover, deuterium was efficiently incorporated into the products.
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