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

✍ Scribed by Dieter Enders; Thomas Hundertmark; Cornelia Lampe; Udo Jegelka; Ilse Scharfbillig

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 229 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199812)1998:12<2839::aid-ejoc2839>3.0.co;2-7

✦ Synopsis

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