TY - JOUR
T1 - Stereoselective formation of functionalized 2-aryl-tetrahydrofurans from aromatic aldehydes via intramolecular 1,3-dipolar cycloadditions (inoc and iooc)
AU - Hassner, Alfred
AU - Rai, K. M.Lokanatha
AU - Dehaen, Wim
N1 - Funding Information:
Acknowledgement: Support of this research by a grant from the US-Israel
PY - 1994/6/1
Y1 - 1994/6/1
N2 - a-Allyloxyaldoximes 8, formed by the reduction of ß-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.
AB - a-Allyloxyaldoximes 8, formed by the reduction of ß-nitrostyrenes 5 with SnCl2-2H20 in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.
UR - http://www.scopus.com/inward/record.url?scp=0028260902&partnerID=8YFLogxK
U2 - 10.1080/00397919408010169
DO - 10.1080/00397919408010169
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AN - SCOPUS:0028260902
SN - 0039-7911
VL - 24
SP - 1669
EP - 1682
JO - Synthetic Communications
JF - Synthetic Communications
IS - 12
ER -