Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans

O-Heterocyclic structures such as 2,3-dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper-catalyzed desymmetrization strategy with a chiral cyclic 1,2-diamine. A broad ran...

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Published inAngewandte Chemie International Edition Vol. 54; no. 30; pp. 8805 - 8808
Main Authors Yang, Wenqiang, Liu, Yangyuan, Zhang, Shasha, Cai, Qian
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 20.07.2015
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Chemistry
Chemistry, Multidisciplinary
Copper
Physical Sciences
Science & Technology
SILYL PROTECTION
PALLADIUM
desymmetrization
ASYMMETRIC-SYNTHESIS
TERT-ALKYLAMINES
3-dihydrobenzofuran
ANALOGS
NATURAL-PRODUCTS
O-arylation
BOND FORMATION
OLEFIN METATHESIS
asymmetric catalysis
ALCOHOLS
2
copper
CYCLIZATION
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Summary:O-Heterocyclic structures such as 2,3-dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper-catalyzed desymmetrization strategy with a chiral cyclic 1,2-diamine. A broad range of substrates are compatible with this Cu-I-diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201503882