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- W2949488568 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." @default.
- W2949488568 created "2019-06-27" @default.
- W2949488568 creator A5074030394 @default.
- W2949488568 date "2008-06-03" @default.
- W2949488568 modified "2023-09-26" @default.
- W2949488568 title "ChemInform Abstract: Basic Instinct: Design, Synthesis and Evaluation of (+)-Sparteine Surrogates for Asymmetric Synthesis" @default.
- W2949488568 cites W1990167275 @default.
- W2949488568 doi "https://doi.org/10.1002/chin.200823223" @default.
- W2949488568 hasPublicationYear "2008" @default.
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