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Ring‐Closing Metathesis of Allylic O , O ‐ and N , O ‐Acetals
Author(s) -
Kinderman Sape S.,
Doodeman Robin,
van Beijma Jetze W.,
Russcher Jaap C.,
Tjen Kim C. M. F.,
Kooistra T. Martijn,
Mohaselzadeh Homayun,
van Maarseveen Jan H.,
Hiemstra Henk,
Schoemaker Hans E.,
Rutjes Floris P. J. T.
Publication year - 2002
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 - 10.1002/1615-4169(200208)344:6/7<736::aid-adsc736>3.0.co;2-8
Subject(s) - chemistry , enantiopure drug , allylic rearrangement , ring closing metathesis , aryl , derivatization , metathesis , acetal , palladium , enantioselective synthesis , ether , medicinal chemistry , alkyl , organic chemistry , catalysis , polymer , polymerization , high performance liquid chromatography
A variety of allylic O,O ‐ and N , O ‐acetals were synthesized using a mild palladium‐catalyzed coupling of an alcohol or sulfonamide with an alkyl or aryl 1,2‐propadienyl ether. The resulting linear acetals were used for the synthesis of unsaturated rings via ring‐closing metathesis, in which the acetal carbon–a precursor for oxycarbenium or N ‐sulfonyliminium ions, respectively–served as a reactive center for further introduction of functional groups. The products–unsaturated oxygen and nitrogen heterocyclic scaffolds–offer multiple opportunities for derivatization as illustrated with the synthesis of substituted dihydropyrans, chromenes, enantiopure tetrahydropyridines and an enantiomerically pure quinolizidine amino acid.