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
Synthesis 2007(18): 2803-2808
DOI: 10.1055/s-2007-983844
DOI: 10.1055/s-2007-983844
PAPER
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of α-Phosphorylated Spiranes
Further Information
Received
1 June 2007
Publication Date:
08 August 2007 (online)
Publication History
Publication Date:
08 August 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200718/lookinside/thumbnails/10.1055-s-2007-983844-1.jpg)
Abstract
α-Oxospiranes have been converted into vinyl triflates for phosphorylation and arylation by palladium-catalyzed cross-coupling reactions. With diethyl phosphite, the coupling provided olefinic mono- and diphosphonated spiranes. Saturation of conjugated aryl and phosphonyl alkene bonds was stereoselective when effected by catalytic hydrogenation. The double bond in conjugated alkenylphosphonates was in general more difficult to reduce than conjugated aryl derivatives. In mixed substrates, regioselectivity in the saturation of conjugated olefinic bonds was obtained.
Key words
spirane-α-phosphonic esters - spirane bridges - cross coupling - phosphorylation - stereoselective hydrogenation
- 1
Rolandsgard M.Baldawi S.Sirbu D.Bjørnstad V.Rømming C.Undheim K. Tetrahedron 2005, 61: 4129 -
2a
Aburel PS.Undheim K. J. Chem. Soc., Perkin Trans. 1 2000, 1891 -
2b
Aburel PS.Rømming C.Undheim K. J. Chem. Soc., Perkin Trans. 1 2001, 1024 - 3
Aburel PS.Rømming C.Ma K.Undheim K. J. Chem. Soc., Perkin Trans. 1 2001, 1458 -
4a
Falck-Pedersen M.-L.Rømming C.Undheim K. Tetrahedron 1999, 55: 8525 -
4b
Sirbu D.Falck-Pedersen ML.Rømming C.Undheim K. Tetrahedron 1999, 55: 6703 - 5
Hartwig JF. In Organopalladium Chemistry for Organic SynthesisNegishi E. Wiley-Interscience; New York: 2002. p.1087 -
6a
Schwan AL. Chem. Soc. Rev. 2004, 33: 218 -
6b
Berthod M.Mignani G.Woodward G.Lemaire M. Chem. Rev. 2005, 105: 1801 -
7a
Hirao T.Masunaga T.Ohshiro Y.Agawa T. Synthesis 1981, 56 -
7b
Holt DA.Erb JM. Tetrahedron Lett. 1989, 30: 5393 -
8a
Uozumi Y.Tanahashi A.Lee SY.Hayashi T. J. Org. Chem. 1993, 58: 1945 -
8b
Kuz L.Lee G.Morgans D.Waldyke MJ.Ward T. Tetrahedron Lett. 1990, 31: 6321 -
9a
Doucet H.Brown JM. Tetrahedron: Asymmetry 1997, 8: 3775 -
9b
Vyskocil S.Smrcina M.Hanaus V.Polasek M.Kocovsky P. J. Org. Chem. 1998, 63: 7738 - 10
Zhou H.Wang W.-H.Fu Y.Xie J.-H.Shi W.-J.Wang L.-X.Zhou Q.-L. J. Org. Chem. 2003, 68: 1582