Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines

Organic Letters

Volumn 13, Issue 13, 2011, Pages 3336-3339

  Olson, David E ^a   Maruniak, Autumn ^a   Malhotra, Sushant ^a   Trost, Barry M ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE; AZIRIDINE DERIVATIVE; DIAMINE; HETEROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AZIRIDINES; CATALYSIS; DIAMINES; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 79959716916     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2010769     Document Type: Article

References (27)

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13. For examples of polyamine-derived natural products, see: Busscher, G. F.; Rutjes, F. P. J. T.; van Delft, F. L. Chem. Rev. 2005, 105, 775-791
14. Differential diamine protection is possible using the diamination method of Shi; see: Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762-763 For the synthesis of differentially protected 1,2-diamines through Rh-catalyzed C-H amination, see: Olson, D. E.; Du Bois, J. J. Am. Chem. Soc. 2008, 130, 11248-11249
15. We refer to these heterocycles as oxathiadiazinanes for simplicity.
16. Prior to our work, we are only aware of one report of these heterocycles; see: Arfaei, A.; Smith, S. J. Chem. Soc., Perkin Trans. 1 1984, 1791-1794
17. For the synthesis and reactivity of related aziridine-fused oxathiazinanes, see: Wehn, P. M.; Du Bois, J. Angew. Chem. 2009, 121, 3860-3863
18. Guthikonda, K.; Wehn, P. M.; Caliando, B. J.; Du Bois, J. Tetrahedron 2006, 62, 11331-11342
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20. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483
21. Compound 2 was prepared using Rh-catalyzed C-H amination; see ref 6.
22. 2. For the initial report of this catalyst, see: Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378-15379
23. The use of i -PrOAc was prompted by a previous report describing aldehyde C-H sulfamidation; see: Chan, J.; Baucom, K. D.; Murry, J. A. J. Am. Chem. Soc. 2007, 129, 14106-14107
24. A similar rationale was put forth to explain diastereoselectivity in analogous reactions involving sulfamides; see: Kurokawa, T.; Kim, M.; Du Bois, J. Angew. Chem., Int. Ed. 2009, 48, 2777-2779
25. Crystallographic data has been deposited at the Cambridge Crystallographic Data Centre (CCDC 809399).
26. Ring opening reactions of bicyclic aziridines such as those featured in Figure 5 are currently limited to azide, cyanide, and thiolate nucleophiles. Reactions performed with oxygen-based nucleophiles (e.g., carboxylates, alkoxides, peroxide) fail to give the desired 7-membered ring product.
27. Olson, D. E.; Roberts, D. A.; Du Bois, J. Manuscript in preparation.