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Highly Diastereo- and Enantioselective Synthesis of Protected anti-1,3-Diols (1998)

Enders, Dieter ; Hundertmark, Thomas ; Lampe, Cornelia ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2839-2849

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ISSN: 1434-193X

Keywords: Asymmetric synthesis ; Hydrazones ; Synthetic methods ; Alkylations ; Deoxygenation ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: An efficient asymmetric synthesis of protected anti-1,3-diols 5 (de ≥ 98%, ee = 92-98%) from 2,2-dimethyl-1,3-dioxan-5-one SAMP hydrazone 1 is described. The key steps are the diastereo- and enantioselective α,α′-bisalkylation followed by reduction of the ketones 2 and a variant of the Barton-McCombie deoxygenation. The new method allows the synthesis of acetonide-protected anti-1,3-diols with a broad range of substituents in good overall yields (31-69%).

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

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