The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9932-9934

  Adams, Harry ^a   Anderson, James C ^a   Peace, Simon ^a   Pennell, Andrew M K ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIAMINE DERIVATIVE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

AMINE TRANSPORT; ARTICLE; CRYSTAL STRUCTURE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032567495     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981700d     Document Type: Article

References (40)

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20. Baldwin, J. E.; Adlington, R. M.; Newington, I. M. J. Chem. Soc., Chem. Commun. 1986, 176-8.
21. This class of product is similar to those that can be obtained by the classic nitro-Mannich reaction [see: Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Groups, Part 2; Patai, S., Ed.; Interscience: New York, 1970; p 117]. However, there are few diastereoisomeric examples, and those that we could find combined N-phenylbenzylimine with either nitroethane (see: Hurd, C. D.; Strong, J. S. J. Am. Chem. Soc. 1950, 72, 4813-4) or nitropropopane (see: Kozlov, L. M.; Fink, E. F. Trudy Kazan. Khim. Tekhnol. Inst. im. S. M. Kirova 1956, 21, 163-6) to yield β-nitro amines both in 35% yield but gave no comment regarding diastereoselectivity.
22. This class of product is similar to those that can be obtained by the classic nitro-Mannich reaction [see: Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Groups, Part 2; Patai, S., Ed.; Interscience: New York, 1970; p 117]. However, there are few diastereoisomeric examples, and those that we could find combined N-phenylbenzylimine with either nitroethane (see: Hurd, C. D.; Strong, J. S. J. Am. Chem. Soc. 1950, 72, 4813-4) or nitropropopane (see: Kozlov, L. M.; Fink, E. F. Trudy Kazan. Khim. Tekhnol. Inst. im. S. M. Kirova 1956, 21, 163-6) to yield β-nitro amines both in 35% yield but gave no comment regarding diastereoselectivity.
23. This class of product is similar to those that can be obtained by the classic nitro-Mannich reaction [see: Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Groups, Part 2; Patai, S., Ed.; Interscience: New York, 1970; p 117]. However, there are few diastereoisomeric examples, and those that we could find combined N-phenylbenzylimine with either nitroethane (see: Hurd, C. D.; Strong, J. S. J. Am. Chem. Soc. 1950, 72, 4813-4) or nitropropopane (see: Kozlov, L. M.; Fink, E. F. Trudy Kazan. Khim. Tekhnol. Inst. im. S. M. Kirova 1956, 21, 163-6) to yield β-nitro amines both in 35% yield but gave no comment regarding diastereoselectivity.
24. Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1101-33.
25. Crystallographic data (excluding structure factors) for structure 6 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101457. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (fax: Int. code +(1223) 336-033; e-mail: deposit@chemcrys.cam.ac.uk).
26. (a) Akhtar, M. S.; Sharma, V. L.; Seth, M.; Bhaduri, A. P. Indian J. Chem. 1988, 27B, 448-51.
27. (b) Sturgess, M. A.; Yarberry, D. J. Tetrahedron Lett. 1993, 34, 4743-6.
28. A forefather of this method for the synthesis of 1,2-diamines is the reduction, with Raney nickel and hydrogen (see Lambert, A.; Rose, J. D. J. Chem. Soc. 1947, 1511-3), of products produced from the condensation between primary (see: Senkus, M. J. Am. Chem. Soc. 1946, 68, 10-12) or secondary amines (see: Johnson, H. G. J. Am. Chem. Soc. 1946, 68, 12-14 and Johnson, H. G. Ibid. 1946, 68, 14-18), formaldehyde, and nitroalkanes. We have found no reports of this method with other aldehydes, which would produce diastereomeric products.
29. A forefather of this method for the synthesis of 1,2-diamines is the reduction, with Raney nickel and hydrogen (see Lambert, A.; Rose, J. D. J. Chem. Soc. 1947, 1511-3), of products produced from the condensation between primary (see: Senkus, M. J. Am. Chem. Soc. 1946, 68, 10-12) or secondary amines (see: Johnson, H. G. J. Am. Chem. Soc. 1946, 68, 12-14 and Johnson, H. G. Ibid. 1946, 68, 14-18), formaldehyde, and nitroalkanes. We have found no reports of this method with other aldehydes, which would produce diastereomeric products.
30. A forefather of this method for the synthesis of 1,2-diamines is the reduction, with Raney nickel and hydrogen (see Lambert, A.; Rose, J. D. J. Chem. Soc. 1947, 1511-3), of products produced from the condensation between primary (see: Senkus, M. J. Am. Chem. Soc. 1946, 68, 10-12) or secondary amines (see: Johnson, H. G. J. Am. Chem. Soc. 1946, 68, 12-14 and Johnson, H. G. Ibid. 1946, 68, 14-18), formaldehyde, and nitroalkanes. We have found no reports of this method with other aldehydes, which would produce diastereomeric products.
31. A forefather of this method for the synthesis of 1,2-diamines is the reduction, with Raney nickel and hydrogen (see Lambert, A.; Rose, J. D. J. Chem. Soc. 1947, 1511-3), of products produced from the condensation between primary (see: Senkus, M. J. Am. Chem. Soc. 1946, 68, 10-12) or secondary amines (see: Johnson, H. G. J. Am. Chem. Soc. 1946, 68, 12-14 and Johnson, H. G. Ibid. 1946, 68, 14-18), formaldehyde, and nitroalkanes. We have found no reports of this method with other aldehydes, which would produce diastereomeric products.
32. Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1991, 32, 1699-1702.
33. Smith, A. B., III; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995-3007.
34. Nitroamines 4 and 7, protected diamines 5 and 8, and diamines 9 have all been fully characterized except for satisfactory elemental analyses. We attribute this to the compounds' sensitivity, but satisfactory elemental analyses were obtained on the di-N-Boc derivatives (see the Supporting Information).
35. -1!
36. 3 as before gave a quantitative recovery of 7 with unaltered diastereomeric excess.
37. a (N-benzylidenebenzylamine) ∼7 (see: Koehler, K.; Sandstrom, W.; Cordes, E. H. J. Am. Chem. Soc. 1964, 86, 2413-9. Cordes, E. H.; Jencks, W. P. Ibid. 1963, 85, 2843-8)
38. a (N-benzylidenebenzylamine) ∼7 (see: Koehler, K.; Sandstrom, W.; Cordes, E. H. J. Am. Chem. Soc. 1964, 86, 2413-9. Cordes, E. H.; Jencks, W. P. Ibid. 1963, 85, 2843-8)
39. a (N-benzylidenebenzylamine) ∼7 (see: Koehler, K.; Sandstrom, W.; Cordes, E. H. J. Am. Chem. Soc. 1964, 86, 2413-9. Cordes, E. H.; Jencks, W. P. Ibid. 1963, 85, 2843-8)
40. For a recent review see: Lucet, D.; LeGall, T.; Mioskowski, C. Angew. Chem., Int. Ed. Engl. 1998, 37, 2580-2627.