Catalytic asymmetric borylative aldol reaction of 5, 6-dihydro-2H-pyran-2-one and ketones. Issue 12 (22nd March 2019)

• Record Type: Journal Article
• Authors: Zhang, Qi; Jia, Xueshun; Yin, Liang
• Is Part Of: Tetrahedron. Volume 75:Issue 12(2019)
• Page Start: 1676
• Page End: 1681
• Publication Date: 2019-03-22
• Subjects: Aldol reaction -- Borylation -- Asymmetric catalysis -- Copper -- Ketone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.11.041
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A copper(I)-catalyzed asymmetric borylative aldol reaction of 5, 6-dihydro-2 H -pyran-2-one and simple ketones (including aromatic ketones and an aliphatic ketone) was disclosed, which afforded a series of chiral diols after an oxidative work-up in moderate yields with moderate to high diastereoselectivity and excellent enantioselectivity. The lactone moiety was easily opened with methanol to generate a chiral triol in moderate yield. Graphical abstract: Image 1