97509-80-3Relevant articles and documents
Stereochemically Controlled Synthesis of Unsaturated Acids by the Coupled Baeyer-Villiger and Horner-Wittig Reactions: Synthesis of (Z)-Oct-6-enoic Acid
Levin, Daniel,Warren, Stuart
, p. 2155 - 2158 (2007/10/02)
The lithium derivative of Ph2P(O)Et reacts with cyclohexene oxide to give largely one diastereoisomer of an alcohol.Oxidation to a ketone and then to a lactone followed by hydrolysis gives a Horner-Wittig intermediate and hence pure (Z)-oct-6-enoic acid.C
Synthesys of Single Isomers (E or Z) of Unsatured Carboxylic Acids by the Horner-Wittig Reaction
Levin, Daniel,Warren, Stuart
, p. 1799 - 1808 (2007/10/02)
Alkyl(diphenyl)phosphine oxides (5) are used to synthesize pure E or Z isomers of unsatured acids.The keto acids (10), made by two routes, are reduced to hydroxy acids whose crystalline lactones (12) can be separated and purified.Stereospecific elimination of Ph2PO2- gives the unsatured acids.
THE STEREOCHEMICALLY CONTROLLED HORNER-WITTIG ROUTE TO UNSATURATED ACIDS: THE BAEYER-VILLIGER REARRANGEMENT OF α-(1-Ph2PO-ALKYL)-CYCLOHEXANONES
Levin, Daniel,Warren, Stuart
, p. 2265 - 2266 (2007/10/02)
Lithiated alkyl diphenylphosphine oxides attack cyclic epoxides with high stereoselectivity: Baeyer-Villiger rearrangement of the derived ketones gives Horner-Wittig intermediates for the synthesis of Z unsaturated acids
STEREOCHEMICALLY CONTROLLED SYNTHESIS OF UNSATURATED ACIDS VIA DIPHENYLPHOSPHINOYL(Ph2PO)-KETOACIDS
Levin, Daniel,Warren, Stuart
, p. 505 - 508 (2007/10/02)
Acylation of phosphine oxide anions with derivatives of cyclic anhydrides or oxidative cleavage of cyclic allyl phosphine oxides gives Ph2PO-ketoacids: reduction, separation of diastereoisomers, and completion of the Horner-Wittig reaction gives single isomers (E or Z) of unsaturated acids.
