1995
DOI: 10.1016/0040-4039(95)00869-e
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First application of the Dakin-West reaction to fmoc chemistry: Synthesis of the ketomethylene tripeptide fmoc-Nα-Asp(tBu)-(R,S Tyr(tBu)Ψ(CO-CH2)Gly-OH

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Cited by 44 publications
(40 citation statements)
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“…Based on the well-documented transformation of Nacyl-or N-Boc-substituted aziridines into oxazolines in the literature [31][32][33][34] and our success 20,21 with the ring-expansion reaction of N-acyl-substituted aziridines with sodium iodide, we envisioned that ring expansion of 1a with (Boc) 2 O in the presence of sodium iodide might be similarly achieved to give oxazolidin-2-one 6a in a one-pot reaction. Thus, we examined the reaction of aziridine 1a with (Boc) 2 O in the presence of sodium iodide in acetone for achieving this aim; however, no reaction occurred, even under refluxing conditions (Table 1, entry 5).…”
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confidence: 99%
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“…Based on the well-documented transformation of Nacyl-or N-Boc-substituted aziridines into oxazolines in the literature [31][32][33][34] and our success 20,21 with the ring-expansion reaction of N-acyl-substituted aziridines with sodium iodide, we envisioned that ring expansion of 1a with (Boc) 2 O in the presence of sodium iodide might be similarly achieved to give oxazolidin-2-one 6a in a one-pot reaction. Thus, we examined the reaction of aziridine 1a with (Boc) 2 O in the presence of sodium iodide in acetone for achieving this aim; however, no reaction occurred, even under refluxing conditions (Table 1, entry 5).…”
mentioning
confidence: 99%
“…Thus, we examined the reaction of aziridine 1a with (Boc) 2 O in the presence of sodium iodide in acetone for achieving this aim; however, no reaction occurred, even under refluxing conditions (Table 1, entry 5).…”
mentioning
confidence: 99%
See 3 more Smart Citations