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Asymmetric Catalytic [4+5] Annulation of ortho ‐Quinone Methides with Vinylethylene Carbonates and its Extension to Stereoselective Tandem Rearrangement
Author(s) -
An XianTao,
Du JiYuan,
Jia ZhiLong,
Zhang Qing,
Yu KeYin,
Zhang YiZhou,
Zhao XianHe,
Fang Ran,
Fan ChunAn
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201904903
Subject(s) - annulation , stereocenter , enantioselective synthesis , tandem , chemistry , claisen rearrangement , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , materials science , composite material
Palladium‐catalyzed asymmetric [4+5] annulation of ortho ‐quinone methides ( o ‐QMs) with substituted vinylethylene carbonates (VECs) is described for the first time, giving a novel enantioselective approach to chiral nine‐membered benzoheterocycles. Based on this designed [4+5] annulation, an unprecedented silica gel‐promoted tandem rearrangement reaction featuring a unique asymmetric aromatic Claisen rearrangement is explored at room temperature, offering a new method for asymmetric construction of all‐carbon quaternary stereocenters embedded in chiral functionalized homoallylic alcohols.