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  • Title: Direct asymmetric catalytic thienylaluminum addition to ketones: a concise approach to the synthesis of (S)-tiemonium iodide.
    Author: Biradar DB, Zhou S, Gau HM.
    Journal: Org Lett; 2009 Aug 06; 11(15):3386-9. PubMed ID: 19588914.
    Abstract:
    A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.
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