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The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products
Abstract
Abstract The reagent formed by combining diethyl azodicarboxylate (DEAD) and triphenylphosphine (TPP) could be utilized in the intermolecular dehydration between an alcohol and various acidic components such as carboxylic acids, phosphoric diesters, imides, and active methylene compounds. By the use of DEAD and TPP, diols and hydroxy acids gave cyclic ethers and lactones, respectively. The reaction of nucleosides with DEAD and TPP afforded triphenylphosphoranylnucleosides. Alcohols reacted with 2,6-di-t-butyl-4-nitrophenol in the presence of DEAD and TPP to give aci-nitroesters which converted into the corresponding carbonyl compounds.
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Cited by
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Zard, S. Z. (1997) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199706721 · Cited by 444
Martin, S. F., & Dodge, J. A. (1991) · Tetrahedron Letters · doi:10.1016/0040-4039(91)80675-v · Cited by 357
Yang, Z., Hutter, D., Sheng, P., Sismour, A. M., & Benner, S. A. (2006) · Nucleic Acids Research · doi:10.1093/nar/gkl633 · Cited by 196
Fluorous phase chemistry: a new industrial technology
Dobbs, A. P., & Kimberley, M. R. (2002) · Journal of Fluorine Chemistry · doi:10.1016/s0022-1139(02)00202-6 · Cited by 131
Metadata
- Authors
- Mitsunobu, O.
- Venue
- Synthesis
- Publisher
- Georg Thieme Verlag KG
- Published
- 1981
- Volume
- 1981
- Issue
- 01
- Pages
- 1-28
- ISSN
- 0039-7881 (ISSN-L)
- 1437-210X
- OpenAlex
- W233628489
- Cited by
- 4,118
- References
- 0
- FWCI
- 35.73
- Type
- journal article
- Language
- en
- Open access
- closed
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