ISSN:
1434-193X
Keywords:
Asymmetric dihydroxylation (Sharpless-AD)
;
Wittig olefination
;
α-Bromo α,β-unsaturated esters
;
Diastereoselective aprotic Michael domino reaction
;
Tricyclo[3.2.1.02,7]octanes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The chiral α-bromo α,β-unsaturated esters 3 and 9 are prepared by asymmetric Sharpless dihydroxylation (AD) of 5 and from ester 7 and the chiral diols 8 by transacetalization, respectively. Both types of α-bromo α,β-unsaturated ester react with the kinetic lithium dienolates of enone 10 to give functionalized tricyclo[3.2.1.02,7]octanes 11. Esters 3 give one single diastereomer (de ≥ 95%), whereas mixtures of diastereomers (de 28 to 46%) are obtained with the esters 9.
Type of Medium:
Electronic Resource
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