101212-36-6Relevant articles and documents
Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary
Klepp, Julian,Podversnik, Harald,Puschnig, Johannes,Wallace, Andrew,Greatrex, Ben W.
, p. 3894 - 3903 (2019)
A family of chiral auxiliaries derived from the lignocellulosic biomass pyrolysis product levoglucosenone (LGO) has been screened in the sulfa-Michael reaction. When promoted by inorganic bases with potassium counterions, the auxiliary with geminal benzyl substituents showed diastereoselectivity up to 90:10 for a broad range of α,β-unsaturated esters.
Total synthesis of jerangolid D
Pospisil, Jiri,Marko, Istvan E.
, p. 3516 - 3517 (2008/01/01)
A short and convergent synthesis of jerangolid D is described. As key steps, a Blaise reaction is employed to construct the lactone ring, a diastereoselective multicomponent Sakurai condensation leads to the dihydropyran ring, and the skipped diene is ass
Baker's yeast mediated biohydrogenation of sulphur-functionalised methacrolein derivatives. Stereochemical aspects of the reaction and preparation of the two enantiomers of useful C4 bifunctional chiral synthons
Serra, Stefano,Fuganti, Claudio
, p. 2191 - 2196 (2007/10/03)
The baker's yeast mediated reduction of sulphur-functionalised methacroleins 11, 15 and 18 leads to the preparation of the bifunctional methyl branched C4 chiral synthons 6 and 7. The stereochemical aspects of the biohydrogenation have been investigated. Both the oxidation state of sulphur and the isomeric position of the double bond affected the enantioselectivity of the reduction strongly, thus, offering access to the two enantiomeric forms of 6 and 7.