Stereospecific synthesis of sec- and tert-alkyl azides from alcohols and trimethylsilyl azide by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite and trimethylsilylmethyl azide

Chemistry Letters

Volumn 37, Issue 10, 2008, Pages 1072-1073

  Mukaiyama, Teruaki ^a   Kuroda, Kiichi ^b   Maruyama, Yuji ^b   Hayashi, Yujiro ^b  

^a KITASATO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67650485297     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2008.1072     Document Type: Article

References (28)

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28. Typical experimental procedure is as follows (Table 2, Entry 5): to PhOPPh2 (0.60 mrnol) in dry toluene (0.30 mL) was added tri-methylsilylmethyl azide (0.60 mrnol) at rt under Ar atmosphere. After this mixture was stirred for 20min at 80 °C, alcohol 1f (0.20 mrnol) in dry toluene (0.60 mL) and TMSN3 (0.60 mmol) were added at rt. The reaction mixture was stirred at rt for 48 h and the crude product was purified by preparative TLC to afford the corresponding azide 2f (86% yield).