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Synfacts 2005(2): 0245-0245  
DOI: 10.1055/s-2005-916125
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Titanium-Mediated Highly Diastereoselective Aldol Reactions

Contributor(s): Paul Knochel, Andrei Gavryushin
J. Solsona, J. Nebot, P. Romea, F. Urpí*
Universidad de Barcelona, Spain
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Publikationsdatum:
25. Oktober 2005 (online)

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Significance

An easily available protected ketone 1 may serve as a building block for the construction of stereochemically controlled aldol products, which are parts of the structures of many natural compounds. A non-toxic and cheap titanium Lewis acid was used to form an enolate for the highly stereoselective aldol reaction. The generated titanium enolate affords highly diaste­reoselective syn,syn-aldol products with a broad range of aldehydes, almost independently of their structure.