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Selective Mono-N-alkylation of 3-Amino Alcohols via Chelation to 9-BBN
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Section:Abstract
A method for selective mono-N-alkylation of amino alcohols is introduced. This method relies on formation of a stable chelate with 9-BBN, which serves in the dual roles of protecting and activating the amine group. Three prototypical amino alcohols featuring various three-carbon bridging units led selectively to the monoalkylated derivatives in very high yields. The straightforward synthesis of the N-CD3 derivatives demonstrates the effectiveness of this approach.
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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Phosphorus−Nitrogen Compounds. 14. Synthesis, Stereogenism, and Structural Investigations of Novel N/O Spirocyclic Phosphazene Derivatives
Elif Ece İlter, Nuran Asmafiliz, and Zeynel Kılıç, Muhammet Işıklan, Tuncer Hökelek, Nagihan Çaylak, Ertan ŞahinInorganic Chemistry2007 46 (23), 9931-9944Phosphorus−Nitrogen Compounds. 14. Synthesis, Stereogenism, and Structural Investigations of Novel N/O Spirocyclic Phosphazene Derivatives
Elif Ece İlter, Nuran Asmafiliz, and Zeynel Kılıç, Muhammet Işıklan, Tuncer Hökelek, Nagihan Çaylak, Ertan ŞahinInorganic Chemistry2007 46 (23), 9931-9944The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N/O donor-type N-alkyl-o-hydroxybenzyl- and o-hydroxynaphthylamines result in novel mono- (3a, 4a and 4b), di- (5a and 5b), and tri- (3b, 6a, and 6b) spirocyclic phosphazene derivatives. ...
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History
- Published In Issue September 30, 2004
- Received July 26, 2004
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