Tetrahedron Letters p. 2373 - 2376 (1995)
Update date:2022-08-10
Topics:
Hirschmann, Ralph
Hynes, John, Jr.
Grant Spoors, P.
Smith, Amos B.
Measurements of H2 evolution revealed that neither 5-trifluoroacetamido-1-pentanol (1) nor 5-acetamido-1-pentanol (6) underwent complete bisdeprotonation upon treatment with excess NaH in THF, thereby accounting for the unexpected course of subsequent alkylations with carbohydrate-derived triflates 2 and 7.These studies in turn led to an effective protocol for generation of N,O-dianions from 1 and 6; as anticipated, the former chemoselectively furnished O-alkylation products with triflates 2 and 15.
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