Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2009(10): 1655-1658
DOI: 10.1055/s-0029-1216634
DOI: 10.1055/s-0029-1216634
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates
Further Information
Received
13 October 2008
Publication Date:
14 April 2009 (online)
Publication History
Publication Date:
14 April 2009 (online)
Abstract
Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl cyanophosphonate to the cyanohydrin phosphate anion.
Key words
phosphonocyanohydrins - diethyl cyanophosphonate - addition reactions - acyl phosphonates - nucleophilic additions
- Supporting Information for this article is available online:
- Supporting Information
- 1
Green TW.Wuts PGM. Protecting Groups in Organic Synthesis 3rd ed.: John Wiley & Sons; New York: 1999. p.348 - 2
Rasmussen JK.Heilmann SM.Krepski LR. Advances in Silicon Chemistry Vol. 1:Larson GL. Jai Press; Greenwich CT: 1991. p.75. - 3
Demir AS.Reis B.Reis O.Eymur S.Gollu M.Tural S.Saglam G. J. Org. Chem. 2007, 72: 7439 - 4
Matsunaga S.Shibasaki M.Yamagiwa N.Abiko Y.Sugita M.Tian J. Tetrahedron: Asymmetry 2006, 17: 566 - 5
Harusawa S.Yoneda R.Kurihara Y.Hamada Y.Shioiri T. Chem. Pharm. Bull. 1983, 31: 3932 - 6a
Fukuda Y.Maeda Y.Kondo K.Aoyama T. Chem. Pharm. Bull. 2006, 54: 397MissingFormLabel - 6b
Abiko Y.Yamagiwa N.Sugita M.Tian J.Matsunaga S.Shibasaki M. Synlett 2004, 2434MissingFormLabel - 7a
Baeza A.Casas J.Najera C.Sansano JM.Saa JM. Angew. Chem. Int. Ed. 2003, 42: 3143MissingFormLabel - 7b
Baeza A.Casas J.Najera C.Sansano JM.Saa JM. Chem. Eur. J. 2005, 3849MissingFormLabel - 8a
Harusawa S.Yoneda R.Kurihara Y. J. Org. Chem. 1991, 56: 1827MissingFormLabel - 8b
Yoneda R.Osaki T.Harusawa S.Kurihara T. J. Chem. Soc., Perkin Trans. 1 1990, 607MissingFormLabel - 8c
Baeza A.Nájera C.Sansano JM. ARKIVOC 2005, (ix): 353MissingFormLabel - 9a
Demir AS.Reis O.Igdir AC.Esiringu I.Eymur S. J. Org. Chem. 2005, 70: 10584MissingFormLabel - 9b
Demir AS.Eymur S. J. Org. Chem. 2007, 72: 8527MissingFormLabel - 9c
Demir AS.Reis O.Esiringu I.Reis B.Baris S. Tetrahedron 2007, 63: 160MissingFormLabel - 9d
Demir AS.Reis O.Kayalar M.Eymur S.Reis B. Synlett 2006, 3329MissingFormLabel - 10a
Okamoto Y.Nitta T.Sakurai H. Bull. Chem. Soc. Jpn. 1969, 42: 543MissingFormLabel - 10b
Pudovik AN.Gur’yanova IV.Banderova LV.Romanov GV. Zh. Obshch. Khim. 1968, 38: 143MissingFormLabel - 10c
Romanov GV.Yafarov MS.Konovalova V.Yusupova TN. Zh. Obshch. Khim. 1973, 43: 2378MissingFormLabel - 11
Konovalova IV.Burnaeva LA.Saifullina NS.Pudovik AN. Zh. Obshch. Khim. 1976, 46: 1410 - 12
Gazizov MB.L’yuis EJ.Kuk AM.Khairullin RA.Kharlamova AG. Zh. Obshch. Khim. 1992, 62: 2548 - 13
Pudovik AN.Romanov GV.Volkova VN. Zh. Obshch. Khim. 1982, 52: 1029