Tetrahedron p. 3851 - 3862 (1986)
Update date:2022-07-30
Topics:
El-Baba, S.
Nuzillard, J. M.
Poulin, J. C.
Kagan, H. B.
Monodehydropeptides with the dehydroaminoacid fragment in C-terminal or N-terminal position were synthetized as well as a family with the general formula Ac-ΔPhe-(Gly)n-Leu-OR (n = 0-2, R = H or Me).Asymmetric reduction of these compounds catalyzed by chiral rhodium complexes was investigated.The results were discussed in terms of double asymmetric induction.A method was developped to avoid the use of both enantiomers of the substrate or of the catalyst, it consists in the total reduction of a racemic dehydropeptide.The products distribution gives access to the two desired facial selectivities.
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