Mitsunobu Reaction

O. Mitsunobu et al., Bull. Chem. Soc. Japan 40, 935 (1967); O. Mitsunobu, Y. Yamada, ibid. 2380.

Condensation of alcohols and acidic components (NuH) on treatment with dialkyl azodicarboxylates and trialkyl- or triarylphosphines occurring primarily with inversion of configuration via the proposed intermediary oxyphosphonium salts:



Methods development: R. F. C. Brown et al., Tetrahedron 50, 5469 (1994); T. Tsunoda et al., Tetrahedron Letters 40, 7355 (1999); J. C. Pelletier, S. Kincaid, ibid. 41, 797 (2000). Synthetic applications: M. A. Poelert et al., Rec. Trav. Chim. 113, 355 (1994); A. Viso et al., Tetrahedron Letters 41, 407 (2000); H. Schedel et al., Tetrahedron Asymmetry 11, 2125 (2000). Solid-phase synthesis: S. R. Chhabra et al., Tetrahedron Letters 41, 1099 (2000); F. Zaragoza, H. Stephensen, ibid. 2015; P.-P. Kung, E. Swayze, ibid. 40, 5651 (1999). Mechanism: T. Watanabe et al., Chirality 12, 346 (2000). Reviews: O. Mitsunobu, Synthesis 1981, 1-28; D. L. Hughes, Org. React. 29, 1-162 (1983); D. L. Hughes, Organic Preparations and Procedures Int. 28, 127-164 (1996); J. A. Dodge, S. A. Jones, Recent Res. Dev. Org. Chem. 1, 273-283 (1997).