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Synthesis and Anionically Induced Domino Reactions of Chiral α-Bromo α,β-Unsaturated Esters (1998)

Braun, Norbert A. ; Bürkle, Ulrike ; Feth, Martin P. ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 1569-1576

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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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