Design, synthesis, and reactivity of 1-hydrazinodienes for use in organic synthesis

Journal of the American Chemical Society

Volumn 127, Issue 24, 2005, Pages 8612-8613

  Sammis, Glenn M ^a   Flamme, Eric M ^a   Xie, Hao ^a   Ho, Douglas M ^a   Sorensen, Erik J ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDRAZINODIENE; ALKADIENE; HYDRAZINE DERIVATIVE; LEWIS ACID; NATURAL PRODUCT; ORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ALKENES; CHEMISTRY, ORGANIC; CYCLIZATION; HYDRAZINES;

EID: 20944438719     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052383c     Document Type: Article

References (22)

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2. For selected reviews and discussions of intermolecular and intramolecular Diels-Alder reactions, see: (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 315-399.
3. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 513-550.
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5. (d) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698.
6. For representative examples, see: (a) Hutchins, R. O.; Kacher, M.; Rua, L. J. Org. Chem. 1975, 40, 923-926.
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10. (e) Myers, A. G.; Zheng, B. Tetrahedron Lett. 1996, 37, 4841-4844.
11. (a) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816-2822.
12. (b) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 20, 981-984.
13. (c) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252-5253.
14. Mono-Alloc hydrazine was synthesized in two steps from tert-butyl carbazate. See the Supporting Information for details.
15. Hydrazinodiene 7 can be stored, in pure form, for extended periods of time at temperatures <0 °C.
16. For a review, see: Guibé, F. Tetrahedron 1998, 54, 2967-3042.
17. Genêt, J. P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S.; Bernard, J. M. Synlett 1993, 680-682.
18. Sulfonylhydrazine 11 was stable to elimination, even when subjected to flash chromatography.
19. The relative stereochemistry was determined from nOe experiments on heterocycle 9a. See Supporting Information for experimental details.
20. The relative stereochemistry was determined via an X-ray crystallographic analysis of 8d.
21. We are currently investigating the nature of the diastereoselectivity for 1-hydrazinodienes in Diels-Alder reactions.
22. Cycloadducts 8g and 8h did not require protection of the esters prior to Alloc deprotection.