Diastereoselective sulfa-Michael reactions controlled by a biomass-derived chiral auxiliary. Issue 29 (19th July 2019)

• Record Type: Journal Article
• Authors: Klepp, Julian; Podversnik, Harald; Puschnig, Johannes; Wallace, Andrew; Greatrex, Ben W.
• Is Part Of: Tetrahedron. Volume 75:Issue 29(2019)
• Page Start: 3894
• Page End: 3903
• Publication Date: 2019-07-19
• Subjects: Chiral auxiliary -- Chiral pool -- Green chemistry -- Levoglucosenone -- Sulfa-Michael addition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.05.051
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: Image 1