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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

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


Authors

A Weber

G Hardy

SV Ley



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.

Acceptance Date Jun 15, 2018
Publication Date Sep 20, 2018
Publicly Available Date Mar 29, 2024
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#!