ISSN:
0947-6539
Keywords:
asymmetric synthesis
;
chirality
;
enolates
;
hydrogen bonds
;
structure elucidation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of acetophenone with tetrabutylammonium hydroxide affords the tetrabutylammonium enolate of phenyl (2-hydroxy-2-phenyl)propyl ketone. The crystal structure of this chiral enolate shows intramolecular hydrogen bonding between the hydroxyl group and the enolate oxygen atom. Furthermore, the α-methylene units of the ammonium counterion form hydrogen bonds to the basic enolate C and O atoms and to the O atom of the hydroxy group. This three-point bonding occurs selectively on the Re,Re side, a phenomenon which may be responsible for the direction of diastereo-selectivity in the epoxide-forming reaction of the enolate with N-bromosuccinimide.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19960020405
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