ISSN:
0947-3440
Schlagwort(e):
Cyclopropanecarboxylates, 2-siloxy-
;
γ-Oxo esters
;
Baeyer-Villiger oxidation
;
Cyclopropanes, absolute configuration of
;
Carbene transfer mechanism
;
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Racemic and enantiomerically enriched methyl 2-siloxycyclopropanecarboxylates 1 have been ring-opened to furnish γ-oxo esters 2. Depending on the electronic properties of substituents, these could be transformed into either succinate derivatives 3 or 3-oxybutanoates 4 by Baeyer-Villiger oxidation. By comparison with known reference compounds the absolute configurations of 3a and 4d, and hence those of their cyclopropane precursors, could be determined. Further literature data on the optical rotations of related cyclopropanes have been collected and compared. A mechanistic interpretation of the asymmetric cyclopropanation of silyl enol ethers based on Pfaltz's model is suggested.
Zusätzliches Material:
2 Tab.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/jlac.199719971014
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