On September 12, 2009, Davies, Stephen G.; Elend, Dirk L.; Jones, Simon; Roberts, Paul M.; Savory, Edward D.; Smith, Andrew D.; Thomson, James E. published an article.Electric Literature of 168297-86-7 The title of the article was The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxy carboxylic acid derivatives and conversion to α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products). And the article contained the following:
The synthesis of α-vinyl-β-hydroxy esters and α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products) via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-iso-Pr SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives α-vinyl-β-hydroxy esters in >98% de and >98% ee. Subsequent isomerization of the double bond into conjugation provides α-ethylidene-β-hydroxy esters (β-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (≥91:9 [(E):(Z)] and >98% ee). The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Electric Literature of 168297-86-7
The Article related to hydroxy ester vinyl ethylidene stereoselective preparation aldol crotonoyloxazolidinone, Aliphatic Compounds: Carboxylic Acids and Peroxycarboxylic Acids and Their Sulfur-Containing Analogs and Salts and other aspects.Electric Literature of 168297-86-7
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem