Journal
ORGANIC LETTERS
Volume 5, Issue 20, Pages 3611-3614Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol035236x
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Chiral phase-transfer catalyst 5 containing an electron-deficient trifluorobenzyl moiety promoted the alkylation of glycine derivative 6 with propargyl bromide 7a in good yield and excellent ee. The resulting propargyl glycine 8 was converted to 14, the central tryptophan residue of Celogentin C, in two steps, with the Pd-catalyzed heteroannulation as the key transformation. This method promises to be an efficient route for the preparation of tryptophan derivatives possessing substitution on the indole ring.
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