Ti(O-isoPr)4 Catalyzed hydrophosphonylation of activated alkenes by diphenyl H-phosphonate

Tetrahedron Letters

Volumn 48, Issue 15, 2007, Pages 2749-2753

  Yao, Qiang ^a  

^a Supresta US LLC   (United States)

Author keywords

Acrylates; Diphenyl H phosphonate; Pudovik reaction; Titanium iso propoxide

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALKANEDIOL DERIVATIVE; ALKENE; METHACRYLIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TITANIUM ALKOXIDE; TITANIUM DERIVATIVE; TITANIUM DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROPHOSPHONYLATION; PUDOVIK REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33947131208     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.055     Document Type: Article

References (19)

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6. For different activation methods of PH addition to C{double bond, long}C or C{triple bond, long}C bonds please see:. Semenzin D., Etemad-Moghadam G., Albouy D., Diallo O., and Koenig M. J. Org. Chem. 62 (1997) 2414-2422
7. We noticed one example using diphenyl H-phosphonate as the hydrophosphonylating agent in special acrylates containing α-lactam ring by using NaH as a catalyst. Hakimelahi G.H., Moosavi-Movahedi A.A., Tsay S.C., Tsai F.Y., Wright J.D., Dudev T., Hakimelahi S., and Lim C. J. Med. Chem. 43 (2000) 3632-3640
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15. Titanium alkoxides have been applied in the hydrophosphonylation of aldehydes by dialkyl H-phosphonates presumably through a metallo-phosphite. Yokomatsu T., Yamagishi T., and Shibuya S. Tetrahedron: Asymmetry 4 (1993) 1779-1782
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17. 3 = 11.87 Hz).
18. 4 also works for diethyl H-phosphonate suggests the proton abstraction from EtOH unlikely because EtOH has weaker acidity than diethyl H-phosphonate.
19. Phenyl acrylate has been shown to be more reactive than methyl acrylate in the base-catalyzed Michael addition. For example,. Shi M., Chen L.H., and Li C.Q. J. Am. Chem. Soc. 127 (2005) 3790-3800