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

Thumbnail
View / Open Files
Authors
Ley, SV
O'Brien, Matthew
Publication Date
2018
Journal Title
Tetrahedron
ISSN
0040-4020
Publisher
Elsevier
Type
Article
Metadata
Show full item record
Citation
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
Rights
Licence:
http://www.rioxx.net/licenses/all-rights-reserved
Statistics



Total file downloads (since January 2020). For more information on metrics see the IRUS guide.