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  • Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione.

Vicinal stereocontrol during nucleophilic addition to arene chromium tricarbonyl complexes: formal synthesis of (+/-)-erythro Juvabione.

Organic letters (2004-06-18)
Anthony J Pearson, Harinandini Paramahamsan, James D Dudones
ABSTRACT

[reaction: see text] Vicinal stereocontrol during nucleophilic addition of tert-butyl lithiopropionate to eta(6)-anisole chromium tricarbonyl complexes with differing para substituents has been studied. Excellent vicinal double stereoinduction (>99:1) was observed when the para substituent was Si(CH(3))(3), and this has been applied to a stereoselective formal synthesis of (+/-)-erythro Juvabione. Asymmetric synthesis by chiral auxiliary directed nucleophilic addition is also discussed.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Hexamethylphosphoramide, purum, ≥98.0% (GC)
Sigma-Aldrich
Hexamethylphosphoramide, 99%
Sigma-Aldrich
Hexamethylphosphoramide, absolute, over molecular sieve (H2O ≤0.03%), ≥98.0% (GC)