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- W2113423144 abstract "Successive treatment of benzyl carbamates 5 (Z-protected secondary amines) with lithium diisopropylamide (LDA), diphenyl phosphorochloridate (DPPC1), and NaN3 yielded the corresponding ã-azidobenzeneacetamides 6 in 45–50% yield (Schemes 2 and 3). In the case of Z-protected diisopropylamine 5b, the phosphate 7 was isolated as a minor product. A reaction mechanism for this unexpected transformation is proposed in Scheme 4, the key step being the ring closure of a benzylic anion to give an oxirane intermediate B. In cursory experiments, it was demonstrated that ã-azidobenzeneacetamides 6 can be used as 2-phenylglycine synthons in the formation of dipeptides by using a phosphine-mediated coupling (Scheme 5)." @default.
- W2113423144 created "2016-06-24" @default.
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- W2113423144 date "1997-11-03" @default.
- W2113423144 modified "2023-09-27" @default.
- W2113423144 title "An unexpected transformation of benzyl carbamates into α-azidobenzeneacetamides" @default.
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- W2113423144 doi "https://doi.org/10.1002/hlca.19970800706" @default.
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