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

Ley, Steven; O'Brien, Matthew

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Authors

Ley, Steven

O'Brien, Matthew

Publication Date

2018-09-20

Journal Title

Tetrahedron

ISSN

0040-4020

Publisher

Elsevier

Type

Article

Metadata

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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

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