Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate

Autor: Piotr Wałejko, Michał Dąbrowski, Lech Szczepaniak, Jacek W. Morzycki, Stanisław Witkowski
Jazyk: angličtina
Rok vydání: 2015
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 11, Iss 1, Pp 1893-1901 (2015)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.11.204
Popis: The ROCM reactions of exo- and endo-2-cyano-7-oxanorbornenes with allyl alcohol or allyl acetate promoted by different ruthenium alkylidene catalysts were studied. The stereochemical outcome of the reactions was established. The issues concerning chemo- (ROCM vs ROMP), regio- (1-2- vs 1-3-product formation), and stereo- (E/Z isomerism) selectivity of reactions under various conditions are discussed. Surprisingly good yields of the ROCM products were obtained under neat conditions.
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