Issue 18, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Allene synthesis by an asymmetric Baylis–Hillman style reaction on vinylphosphine oxides

David J. Fox,a   Jonathan A. Medlock,a   Richard Vossera  and  Stuart Warren*a  

* Corresponding authors

a University Chemical Laboratory, Lensfield Road, Cambridge, UK
E-mail: sw134@cam.ac.uk

Abstract

A novel reaction has been discovered with a mechanism similar to the Baylis–Hillman reaction. Reaction of a vinylic phosphine oxide with (R)-N-lithio-α-methylbenzylbenzylamine 2 in the presence of an aldehyde gave hydroxyphosphine oxides in good to moderate yields and moderate to poor enantioselectivities. The hydroxyphosphine oxides undergo the Horner–Wittig elimination reaction to produce allenes. Baylis–Hillman reactions of vinylic phosphine oxides with tertiary amines were also investigated.

Graphical abstract: Allene synthesis by an asymmetric Baylis–Hillman style reaction on vinylphosphine oxides

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B104436M
Article type
Paper
Submitted
21 May 2001
Accepted
18 Jul 2001
First published
15 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2240-2249

Permissions

Request permissions

Allene synthesis by an asymmetric Baylis–Hillman style reaction on vinylphosphine oxides

D. J. Fox, J. A. Medlock, R. Vosser and S. Warren, J. Chem. Soc., Perkin Trans. 1, 2001, 2240 DOI: 10.1039/B104436M

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements