A Stereoselective and Atom-Efficient Approach to
Multifunctionalized Five- and Six-Membered Rings via a Novel
Michael-Initiated Intramolecular Diels−Alder Furan Reaction
Irishi N. N. Namboothiri
Madhu Ganesh
Shaikh M. Mobin
Miriam Cojocaru
10.1021/jo048262x.s001
https://acs.figshare.com/articles/dataset/A_Stereoselective_and_Atom_Efficient_Approach_to_Multifunctionalized_Five_and_Six_Membered_Rings_via_a_Novel_Michael_Initiated_Intramolecular_Diels_Alder_Furan_Reaction/3295822
A variety of key precursors to the intramolecular Diels−Alder reaction of furan diene (IMDAF)
have been prepared via a very facile 1,4-addition of O-, S-, N-, and C-centered nucleophiles possessing
unsaturated tether to β-furyl nitroethylene. Subsequent IMDAF reaction of the 1,4-adducts, carried
out under thermal conditions, provided five- and six-membered carbocycles and heterocycles fused
to an easily cleavable oxabicycloheptene moiety. The structure and stereochemistry of the
cycloadducts were determined by 2D-NMR experiments and further confirmed by X-ray crystallography. The salient features of the strategy include high degree of stereoselectivity (>80:20) in
the cycloaddition, atom and step economy, and generation of multiple chiral centers and
functionalities. The feasibility of the cleavage of the oxa bridge in the cycloadducts to afford novel
multifunctional molecules has also been demonstrated.
2005-03-18 00:00:00
furan diene
step economy
cleavage
generation
feasibility
intramolecular
tether
crystallography
cycloaddition
experiment
Furan
novel multifunctional molecules
chiral centers
precursor
Stereoselective
adduct
oxa bridge
Approach
strategy
Diel
heterocycle
functionalitie
stereoselectivity
cycloadduct
nitroethylene
cleavable oxabicycloheptene moiety
Subsequent IMDAF reaction
variety
Multifunctionalized
stereochemistry
carbocycle
furyl
nucleophile
Intramolecular