The facile synthesis of a series of tryptophan derivatives
This study reports a facile method for the synthesis of a variety of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions provides some insights into the likely mechanism of the reaction.
Blaser, Georg,Sanderson, John M.,Batsanov, Andrei S.,Howard, Judith A.K.
p. 2795 - 2798
(2008/09/19)
Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the lewis acid
(Chemical Equation Presented) Highly regioselective electrophilic substitution of indoles with N-acetylated α,β-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient p
Angelini, Elena,Balsamini, Cesarino,Bartoccini, Francesca,Lucarini, Simone,Piersanti, Giovanni
p. 5654 - 5657
(2008/12/21)
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