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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.

ABSTRACT: 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.

SUBMITTER: Walejko P

PROVIDER: S-EPMC4661012 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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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.

Wałejko Piotr P Dąbrowski Michał M Szczepaniak Lech L Morzycki Jacek W JW Witkowski Stanisław S

Beilstein journal of organic chemistry 20151013

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. ...[more]

PMID: 26664608

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