ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A stereoselective synthesis of tricarbonyl-[((1RS,2RS,4RS,5RS,6RS)-C-5,6,C-η-(5,6,7,8,-tetramethylidenbicyclo[2.2.2]octan-2-ol)]iron (11),and of its tosylate 12 and benzoate 13 is reported. The bulk of the ‘endo’-Fe(CO))3 moiety and of the ester groups in 13 renders its Diels-Alder additions to methyl propynoate (15)), butynone (16), and 1-cyanovinyl acetate highly ‘para’ regioselective. The cycloadditions of diene-alcohol 11 are either ‘meta’- or ‘para’-regioselective depending on the nature of the dienophile. In the presence of BF3. Et2O, the addition of 11 to methyl vinyl ketone is highly stereo- (Alder mode) and ‘para’-regioselective, giving adduct 52 (tricarbonyl [((1 RS,4RS,8RS,9RS,10RS,12RS)-C,9,10,C-η-(12-hydroxy-9,10-dimethylidenetricyclo[6.2.2.02,7]dodec-2(7)-en-4 yl methyl ketone)]iron) whose structure has been established by single-crystal X-ray crystallography.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700502
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