71699-33-7Relevant articles and documents
Stereoselective synthesis of a novel spiroacetal-dihydropyrone related to auripyrone
Perkins, Michael V.,Jahangiri, Saba,Taylor, Max R.
, p. 2025 - 2028 (2006)
A model spiroacetal-dihydropyrone related to that found in auripyrones A and B has been synthesised by a spiroacetalisation dehydration cascade. The route includes an unusual mutual kinetic diastereoselecting aldol reaction combining the key fragments.
Lithium hexamethyldisilazide-mediated enolizations: Influence of triethylamine on E/Z selectivities and enolate reactivities
Godenschwager, Peter F.,Collum, David B.
supporting information; experimental part, p. 8726 - 8732 (2009/02/02)
Lithium hexamethyldisilazide (LiHMDS) in triethylamine (Et 3N)/toluene is shown to enolize acyclic ketones and esters rapidly and with high E/Z selectivity. Mechanistic studies reveal a dimer-based mechanism consistent with previous studies of
Stereoselective aldol reaction of α-seleno carbonyl compounds: Preparation of (Z)-α,β-unsaturated carbonyl compounds
Nakamura, Shuichi,Hayakawa, Toshinobu,Nishi, Tatsuya,Watanabe, Yoshihiko,Toru, Takeshi
, p. 6703 - 6711 (2007/10/03)
The aldol reaction of the titanium enolates of α-seleno esters in the presence of Ph3P or Ph3PO gave the products with high stereoselectivity favoring the syn isomers. Reaction of α-seleno ketones with TiCl4 in the presence of 2 equiv. of Et3N, and subsequently with aldehydes, gave the aldol products with high syn selectivity. The stereoselectivity in the aldol reaction of 3-pentanone also increased by using an excess amount of Et3N. The aldol products thus obtained from the α-seleno carbonyl compounds could be stereospecifically converted to (Z)-α,β-unsaturated carbonyl compounds by treatment with pyridine. (Z)-Alkylidenecyclopentanones were exclusively formed by treatment of the syn-aldol products with Et3N in the dark.
