One-pot conversion of azides to Boc-protected amines with trimethylphosphine and Boc-ON

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9101-9102

  Ariza, Xavier ^a   Urpí, Fèlix ^a   Viladomat, Carles ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Amines; Azides; Carbamates; Phosphazenes; Protecting groups

Indexed keywords

AMINE; AZIDE; PHOSPHINE DERIVATIVE; TOLUENE;

ARTICLE; CATALYSIS; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0032481022     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02006-1     Document Type: Article

References (15)

1. [1] Greene TW, Wuts PGM. Protective Groups in Organic Synthesis, Wiley: New York, 1991. Kocienski PJ. Protecting Groups, Thieme: Stuttgart, 1994. Encyclopedia of Reagents for Organic Synthesis. Paquette LA, ed. Vol. 3. Wiley: Chichester, 1995.
2. [1] Greene TW, Wuts PGM. Protective Groups in Organic Synthesis, Wiley: New York, 1991. Kocienski PJ. Protecting Groups, Thieme: Stuttgart, 1994. Encyclopedia of Reagents for Organic Synthesis. Paquette LA, ed. Vol. 3. Wiley: Chichester, 1995.
3. [1] Greene TW, Wuts PGM. Protective Groups in Organic Synthesis, Wiley: New York, 1991. Kocienski PJ. Protecting Groups, Thieme: Stuttgart, 1994. Encyclopedia of Reagents for Organic Synthesis. Paquette LA, ed. Vol. 3. Wiley: Chichester, 1995.
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5. 2O: Woltering TJ, Weiz-Schmidt G, Wong CH. Tetrahedron Lett. 1996;37:9033-9036.
6. 2O (1.5 equiv), mixing all together in EtOH, to obtain the corresponding Bocamines in 64-99% yields; although a conjugate double bond survived, in another example a phenolic benzyl group did not.
7. [5] Afonso CAM. Tetrahedron Lett. 1995;36:8857-8858. Full paper: Afonso CAM. Synth. Commun. 1998;28: 261-276.
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14. [8] Under these conditions phosphatriazene intermediates may be involved (Bosch I, Urpí F, Vilarrasa J. J. Chem. Soc. Chem. Commun. 1995; 91-92).
15. 3P the reactions are much slower and the yields lie only around 60%.