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Issue 6, 2008
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Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis

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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

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

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

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