Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone

O'Brien, M; Weber, A; Hardy, G; Ley, SV

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.

Citation

O'Brien, M., Weber, A., Hardy, G., & Ley, S. (2018). Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone. Tetrahedron, 5319 - 5329. https://doi.org/10.1016/j.tet.2018.06.041

• Acceptance Date: Jun 15, 2018
• Publication Date: Sep 20, 2018
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Pages: 5319 - 5329
• DOI: https://doi.org/10.1016/j.tet.2018.06.041
• Keywords: Aldol; Diastereoselectivity; Butane-diacetal
• Publisher URL: https://www.sciencedirect.com/science/article/pii/S0040402018307415?via%3Dihub#!