4.8 Article

Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels-Alder Reaction

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 16, 页码 5625-+

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ja1018628

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资金

  1. NSF [CHE-0717618]
  2. MEXT [21750096]
  3. Asahi Glass Foundation
  4. Grants-in-Aid for Scientific Research [21750096] Funding Source: KAKEN

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Highly enantioselective Diels-Alder reactions of alpha-halo-alpha,beta-unsaturated ketones with Lewis acid-activated chiral oxazaborolidine 1 are described. The reaction with alpha-fluoroenones provided the corresponding cyclohexane derivatives having a fluorinated quaternary stereogenic center with up to 99% de and 94% ee. The reaction with alpha-bromo cyclic enones provided the corresponding bromo bicyclic adducts with up to 99% de and 95% ee. A brominated cis-fused bicyclic adduct derived from 2-bromocyclopenten-1-one and Dane's diene was converted to the trans-fused bicyclic system via reductive alkylation with the bulky aluminum reagent aluminum tris(2,6-diphenylphenoxide) (ATPH). With this process, formal syntheses of (+)-estrone and norgestrel have been demonstrated.

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