One-Pot Enantioselective Synthesis of Tryptophan Derivatives via Phase-Transfer Catalytic Alkylation of Glycine Using a Cinchona-Derived Catalyst

[摘要]：Tryptophans are building blocks for many natural products. This paper describes the enantiospecific synthesis of ring-A substituted tryptophan derivatives from commercially available gramines using chiral phase-transfer conditions. This one-pot reaction avoids protecting/deprotecting the indolylic nitrogen of gramine by choosing a chemoselective quaternization reagent, 4-(trifluoromethoxy)benzyl bromide, to produce an electrophilic salt intermediate, which is subsequently alkylated in good yield with high enantiomeric excess.

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