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Grignard Reagent Acceleration of the Intramolecular Diels–Alder Reaction of Furans with Unactivated Alkynes: Towards Structurally Complex Oxabicyclic Alkenes
Author(s) -
Chen Yifeng,
Wang Lu,
Liu Yuanhong,
Li Yuxue
Publication year - 2011
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.201102028
Subject(s) - intramolecular force , chemistry , reagent , stereoselectivity , alkoxide , diels–alder reaction , magnesium , grignard reagent , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis
Chelate to accelerate : A cascade reaction of ortho ‐(alkynyl)phenyl furanyl ketones with Grignard reagents, involving an interesting intramolecular Diels–Alder reaction of furans with unactivated alkynes, is described (see scheme). DFT calculations and experimental results suggest that the formation of a chelated magnesium alkoxide plays an important role in accelerating the reaction rate and determining the stereoselectivity.