Asymmetric aldol reaction using boron enolates

Loading...
Thumbnail Image
File version
Author(s)
Cergol, Katie M
Coster, Mark J
Griffith University Author(s)
Primary Supervisor
Other Supervisors
Editor(s)
Date
2007
Size

165149 bytes

File type(s)

application/pdf

Location
License
Abstract

The protocol for the preparation of boron enolates and their subsequent reaction with aldehydes is described, providing convenient access to ߭hydroxy ketones in good yields and with high stereoselectivities. The reaction consists of three steps; firstly the ketone is rapidly converted to the corresponding boron enolate, by exposure to a chlorodialkylborane and tertiary amine base, which is then reacted in situ with the aldehyde. Finally, oxidative workup of the resultant boron aldolate provides aldol adduct. The reaction procedure requires approximately 28 h to complete over a two day period, consisting of 5 h to set up the reaction, whereupon the reaction mixture is left at -20 àovernight (16 h), followed by 7 h for workup and purification.

Journal Title

Nature Protocols

Conference Title
Book Title
Edition
Volume

2

Issue

10

Thesis Type
Degree Program
School
Patent number
Funder(s)
Grant identifier(s)
Rights Statement
Rights Statement

© 2007 Nature Publishing Group. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.

Item Access Status
Note
Access the data
Related item(s)
Subject

Chemical sciences

Biological sciences

Biomedical and clinical sciences

Persistent link to this record
Citation
Collections