Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2, 3-butanediacetal ethyl ketone. Issue 38 (20th September 2018)

• Record Type: Journal Article
• Authors: O'Brien, Matthew; Weber, Arne; Hardy, Gemma; Ley, Steven V.
• Is Part Of: Tetrahedron. Volume 74:Issue 38(2018)
• Page Start: 5319
• Page End: 5329
• Publication Date: 2018-09-20
• Subjects: Aldol -- Diastereoselectivity -- Butane-diacetal; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.06.041
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A mannitol derived 2, 3-butanediacetal ethyl ketone displays high levels of diastereoselectivity in boron and titanium mediated aldol reactions with a range of aliphatic and aromatic aldehydes to afford syn aldol products in high yield. The stereochemical outcome of the reaction was determined using J -value analysis, NMR analysis of O -acetylmandelate derivatives and X-ray crystallography. Graphical abstract: Image 1