ISSN:
0947-6539
Keywords:
aggregates
;
asymmetric syntheses
;
stereochemistry
;
sulfoximines
;
zinc enolates
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The preparation, structural characterization, and reactivity of ethylzinc-containing enolates and organometallics derived from β-carbonyl sulfoximines are reported. X-ray crystal structures show significant differences between aggregated species obtained from β-keto and β-amido sulfoximines. Whereas the former gives an O-metalated ethylzinc enolate, the latter crystallizes as C-metalated carbonyl species. NMR investigations reveal the presence of chelated zinc enolates in solution. The relationship between structure and reactivity is demonstrated by the reaction profiles of the ethylzinc-containing compounds. A high diastereoselectivity (〉 90% de) was observed in the aldol reaction between the metalated β-amido sulfoximine and benzaldehyde in the presence of trimethylsilyl chloride.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19950010508
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