ISSN:
0009-2940
Keywords:
Ring enlargement
;
Phellandrene
;
Carbonylation
;
Bicyclo[3.2.1]octanes, stereoselective syntheses of
;
Iron complexes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Carbonylating Ring Enlargement, 41). - Diastereoselective Syntheses of Bicyclo[3.2.l]oct-3-ene-2,8-diones by Double Carbonylation of (It)-(-)-α-PhellandreneIn order to clarify the stereochemistry of the carbonylating ring enlargement of cyclohexadiene complexes 1 to complexed seven-membered ring ketones 2 and the further carbonylation to bicyclo[3.2.1]oct-3-ene-2,8-diones 3 the exo and endo isomers of (R)-(-)-α-phellandrene complex 7 were synthesized in pure form and in various isomeric ratios and converted. The optically active ring-enlargement products 11 and 12 obtained therefrom, as well as the enantiomerically pure bicyclooctenes 20-22, implicate a stereospecific reaction course under retention of the configuration predetermined by the starting material 6 and its complexes 7. This was confirmed by an X-ray determination of the absolute configuration of exo-12. Thus, the method is suitable for the diastereoselective synthesis of bicyclo[3.2.1]oct-3-ene-2,8-diones 3 from 1,3-cyclohexadiene complexes 1.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19901230522
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