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Synlett 2001; 2001(Special Issue): 1016-1018
DOI: 10.1055/s-2001-14650
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Pentadienyltitaniums as Versatile Intermediates: Regio- and Stereoselectivities

Armin Zellner* , Manfred Schlosser
  • *Section de Chimie, Université, BCh, CH-1015 Lausanne, Switzerland; Fax + 41-21-6 92 39 65; E-mail: manfred.schlosser@ico.unil.ch
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Publication History

Publication Date:
31 December 2001 (online)

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The adduct obtained upon consecutive treatment of 1,4-dienes with butyllithium in the presence of potassium tert-butoxide, chlorotri(isopropyloxy)titanium and a carbonyl compound contains the α-hydroxyalkyl group invariably and exclusively linked to the 3-position of the former diene. When chlorotri(isopropyloxy)titanium is replaced by the Duthaler-Hafner reagent [4R,5R)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O α )titanium] the reaction does not only occur regioselectively but also with appreciably high enantioselectivity.

superbase - metal effects - regioselectivity of electrophilic attack - stereoselectivity of carbon-carbon bond formation - natural product synthesis

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