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Synthesis 1997; 1997(8): 967-974
DOI: 10.1055/s-1997-1294
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Efficient Approaches to the Stereoselective Synthesis of Chiral 2-Alkoxydienes and Heterodienes

José Barluenga* , Miguel Tomás, Luis A. López, Angel Suárez-Sobrino
  • *Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, 33071-Oviedo, Spain, Fax +34(8)5103450; E-mail: barluenga@sauron.quimica.uniovi.es
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Publication Date:
31 December 2000 (online)

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Three approaches to dienes having a chiral alkoxy group at C-2 are shown. Alkoxypropenylphosphonium salts 3 undergo stereoselective Wittig reaction affording high yields of racemic and/or homochiral 2-menthyloxy-, 2-(8-phenylmenthyloxy)-, 2-trans-phnylcyclohexyloxy- and 2-trans-mesitylcyclohexyloxybuta-1,3-dienes 5a-j (Method A). Esters derived from chiral alcohols 6 are methylenated with dimethyltitanocene to yield chiral dienes 5a, e, 7 (Method B). Chiral α-alkoxyacroleins 8 are prepared by the aza-Wittig reaction of 3 followed by imine hydrolysis and utilized for synthesizing various types of activated chiral alkoxycarbodienes 10, 12 and 14 (Method C), as well as 3-alkoxy-1-azabutadiene derivatives 15.

2-alkoxy-1,3-butadienes - 2-alkoxyacroleins - 3-alkoxy-1-aza-1,3-butadienes - Wittig olefination - methylenation