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 2024; 56(12): 1843-1850
DOI: 10.1055/a-2232-8633
DOI: 10.1055/a-2232-8633
short review
Mechanism of the Mitsunobu Reaction: An Ongoing Mystery
We thank the National Institutes of Health (NIH; grant R01GM071779) for financial support.
Abstract
The Mitsunobu reaction is one the most widely known reactions in the organic chemistry canon. Despite its fame, some aspects of the mechanism remain poorly understood, 55 years after its initial discovery. This short review collates the findings of several publications focused on the mechanism of the Mitsunobu reaction, highlighting both the current state of knowledge and the remaining missing pieces.
1 Introduction
2 Mechanism Overview
3 Mechanistic Investigations
4 Conclusion
Publication History
Received: 14 November 2023
Accepted after revision: 19 December 2023
Accepted Manuscript online:
19 December 2023
Article published online:
24 January 2024
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Mitsunobu O, Yamada M. Bull. Chem. Soc. Jpn. 1967; 40: 2380
- 2 Mitsunobu O. Synthesis 1981; 1
- 3 Ertl P. Bioorg. Med. Chem. 2022; 54: 116562
- 4 Swamy KC. K, Kumar NN. B, Balaraman E, Kumar KV. P. P. Chem. Rev. 2009; 109: 2551
- 5a But TY. S, Toy PH. J. Am. Chem. Soc. 2006; 128: 9636
- 5b Hirose D, Taniguchi T, Ishibashi H. Angew. Chem. Int. Ed. 2013; 52: 4613
- 5c Buonomo JA, Aldrich CC. Angew. Chem. Int. Ed. 2015; 54: 13041
- 5d Hirose D, Gazvoda M, Košmrlj J, Taniguchi T. Chem. Sci. 2016; 7: 5148
- 5e Hirose D, Gazvoda M, Košmrlj J, Taniguchi T. Org. Lett. 2016; 18: 4036
- 5f Beddoe RH, Sneddon HF, Denton RM. Org. Biomol. Chem. 2018; 16: 7774
- 5g Beddoe RH, Andrews KG, Magné V, Cuthbertson JD, Saska J, Shannon-Little AL, Shanahan SE, Sneddon HF, Denton RM. Science 2019; 365: 910
- 5h Zou Y, Wong JJ, Houk KN. J. Am. Chem. Soc. 2020; 142: 16403
- 6a Grochowski E, Hilton BD, Kupper RJ, Michejda CJ. J. Am. Chem. Soc. 1982; 104: 6876
- 6b Grochowski E. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1980; 28: 489
- 7 Varasi M, Walker KA. M, Maddox ML. J. Org. Chem. 1987; 52: 4235
- 8a Camp D, Jenkins ID. J. Org. Chem. 1989; 54: 3045
- 8b Camp D, Jenkins ID. J. Org. Chem. 1989; 54: 3049
- 9 Hughes DL, Reamer RA. J. Org. Chem. 1996; 61: 2967
- 10 Ahn C, Correia R, DeShong P. J. Org. Chem. 2002; 67: 1751
- 11 Watanabe T, Gridnev ID, Imamoto T. Chirality 2000; 12: 346
- 12a Berry RS. J. Chem. Phys. 1960; 32: 933
- 12b Gutowsky HS, McCall DW, Slichter CP. J. Chem. Phys. 1953; 21: 279
- 13 Hughes DL, Reamer RA, Bergan JJ, Grabowski EJ. J. J. Am. Chem. Soc. 1988; 110: 6487
- 14 Pautard-Cooper A, Evans SA. Jr. J. Org. Chem. 1989; 54: 2485
- 15 Macor JE, Wehner JM. Heterocycles 1993; 35: 349
- 16 Crich D, Dyker H, Harris RJ. J. Org. Chem. 1989; 54: 257
- 17 Wilson SR, Perez J, Pasternak A. J. Am. Chem. Soc. 1993; 115: 1994
- 18 Dodge JA, Trujillo JI, Presnell M. J. Org. Chem. 1994; 59: 234
- 19 Mulzer J, Brüntrup G, Chucholowski A. Angew. Chem., Int. Ed. Engl. 1979; 18: 622
- 20 Kodaka M, Tomohiro T, Okuno H. J. Chem. Soc., Chem. Commun. 1993; 81
- 21 McNulty J, Capretta A, Laritchev V, Dyck J, Robertson AJ. Angew. Chem. Int. Ed. 2003; 42: 4051
- 22 Camp D, Harvey PJ, Jenkins ID. Tetrahedron 2015; 71: 3932
- 23 Camp D, von Itzstein M, Jenkins ID. Tetrahedron 2015; 71: 4946
- 24 Schenk S, Weston J, Anders E. J. Am. Chem. Soc. 2005; 127: 12566
- 25a Swamy KC. K, Kumar KP, Kumar NN. B. J. Org. Chem. 2006; 71: 1002
- 25b Kumar NS, Kommana P, Vittal JJ, Swamy KC. K. J. Org. Chem. 2002; 67: 6653
- 25c Kumar NS, Kumar KP, Kumar KV. P. P, Kommana P, Vittal JJ, Swamy KC. K. J. Org. Chem. 2004; 69: 1880
- 25d Kumar KV. P. P, Kumar NS, Swamy KC. K. New J. Chem. 2006; 30: 717
- 26 Heesing A, Steinkamp H. Chem. Ber. 1982; 115: 2854