Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 6, 2008
Previous Article Next Article

Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis

Author affiliations

Abstract

(–)-Sparteine, a naturally occurring lupin alkaloid, is widely used as a chiral ligand for asymmetric synthesis. To address the limitation that sparteine is only available as its (–)-antipode, our group introduced a family of (+)-sparteine surrogates that are structurally similar to (+)-sparteine but lack the D-ring. After briefly summarising the design aspect, this feature article provides an overview of synthetic routes to the sparteine surrogates and a detailed comparison with (–)-sparteine in a range of asymmetric reactions. The main conclusions are: (i) the (+)-sparteine surrogates are most easily prepared starting from (–)-cytisine extracted from Laburnum anagyroides seeds; (ii) in nearly all examples, use of the (+)-sparteine surrogates produced essentially equal but opposite enantioselectivity compared to (–)-sparteine and (iii) the N-Me-substituted (+)-sparteine surrogate is the most useful and versatile of those investigated.

Graphical abstract: Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis

Back to tab navigation
Please wait while Download options loads

Publication details

The article was received on 26 Jul 2007, accepted on 26 Sep 2007 and first published on 16 Oct 2007


Article type: Feature Article
DOI: 10.1039/B711420F
Citation: Chem. Commun., 2008, 655-667
  •   Request permissions

    Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis

    P. O'Brien, Chem. Commun., 2008, 655
    DOI: 10.1039/B711420F

Search articles by author