- Asymmetric synthesis of the cis- And trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid
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The diastereoselective conjugate addition of lithium (S)-N-benzyl-N- α-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and fraBs-(3R,4R)-4-arninotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.
- Bunnage, Mark E.,Davies, Stephen G.,Roberts, Paul M.,Smith, Andrew D.,Withey, Jonathan M.
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p. 2763 - 2776
(2007/10/03)
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