Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone
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Publication Date
2018-09-20Journal Title
Tetrahedron
ISSN
0040-4020
Publisher
Elsevier
Type
Article
Metadata
Show full item recordCitation
Ley, S., & O'Brien, M. (2018). Highly diastereoselective boron and titanium mediated aldol reactions of a mannitol derived 2,3-butanediacetal ethyl ketone. Tetrahedron https://doi.org/10.1016/j.tet.2018.06.041
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 acetoxymandelate
derivatives and X-ray crystallography.
Keywords
aldol, diastereoselectivity, butane-diacetal
Identifiers
External DOI: https://doi.org/10.1016/j.tet.2018.06.041
This record's URL: https://www.repository.cam.ac.uk/handle/1810/279622
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