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Oxidative Catalytic Spiroketalization Leading to Diastereoselective Synthesis of Spiro[benzofuran‐2,1′‐isochromene]s
Author(s) -
Qiu JiangKai,
Hao WenJuan,
Li Guigen,
Jiang Bo
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701149
Subject(s) - chemistry , benzofuran , catalysis , imine , substrate (aquarium) , aryl , medicinal chemistry , alkyl , oxidative phosphorylation , quinone , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , oceanography , geology
A new one‐pot, two‐step silver‐catalyzed spiroketalization of the in‐situ generated quinone imine ketals (QIKs) with β‐alkynyl ketones has been established, enabling multiple C−O and C−C bond‐forming reactions to access densely functionalized spiro[benzofuran‐2,1′‐isochromene] derivatives with generally good yields. The use of β ‐alkynyl ketones bearing alkyl and aryl groups located at the α‐position of the carbonyl group could lead to highly diastereoselective spiro[chromane‐2,1′‐isochromene] derivatives. The reaction features broad substrate scope, mild oxidative catalytic conditions and excellent diastereoselectivity.