Journal
TETRAHEDRON LETTERS
Volume 47, Issue 23, Pages 3843-3847Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2006.03.183
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beta(3)-Homoamino acids catalyze the intra- (cf. the Hajos-Parrish-Eder-Sauer-Wiechert reaction) as well as the intermolecular aldol reaction. The stereochemical outcome with selectivities of up to 83% ee is reversed in the intramolecular reaction, when we go from the proteinogenic amino acids to the homologues, and reaction time increases dramatically for both reactions. In contrast, in the intermolecular reaction Me-beta(3)hPhe-OH gives the same enantiomer as (S)-proline does, but with lower enantiomeric excess (54% vs 48% ee). (c) 2006 Elsevier Ltd. All rights reserved.
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