New synthetic technology for the rapid construction of novel heterocycles - Part 1: The reaction of Dess - Martin periodinane with anilides and related compounds

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 622-625

  Nicolaou, K C ^a   Zhong, Yong Li ^a   Baran, Phil S ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILIDE; HETEROCYCLIC COMPOUND; IODINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR MODEL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034603046     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000204)39:3<622::AID-ANIE622>3.0.CO;2-B     Document Type: Article

References (20)

1. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774-1781; Angew. Chem. Int. Ed. 1999, 38, 1669-1675; K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781-1784; Angew. Chem. Int. Ed. 1999, 38, 1676-1678.
2. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774-1781; Angew. Chem. Int. Ed. 1999, 38, 1669-1675; K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781-1784; Angew. Chem. Int. Ed. 1999, 38, 1676-1678.
3. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774-1781; Angew. Chem. Int. Ed. 1999, 38, 1669-1675; K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781-1784; Angew. Chem. Int. Ed. 1999, 38, 1676-1678.
4. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774-1781; Angew. Chem. Int. Ed. 1999, 38, 1669-1675; K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781-1784; Angew. Chem. Int. Ed. 1999, 38, 1676-1678.
5. a) D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156;
6. b) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7278;
7. c) S. D. Meyer, S. L. Schreiber, J. Org. Chem. 1994, 59, 7549-7552.
8. Compounds 3b and 4b are formed as single regioisomers, whereas 5b and 6b are mixtures. Efforts to understand this peculiar finding are underway.
9. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133866. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (x 44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
10. S. Patai, The Chemistry of Cyanates and Their Derivatives, Wiley, Chichester, 1977; S. Ozaki, Chem. Rev. 1972, 72, 457-496.
11. S. Patai, The Chemistry of Cyanates and Their Derivatives, Wiley, Chichester, 1977; S. Ozaki, Chem. Rev. 1972, 72, 457-496.
12. a) A. Varvoglis, S. Spyroudis, Synlett 1998, 221-232;
13. b) Hypervalent Iodine in Organic Synthesis (Ed.: A. Varvoglis). Academic Press, San Diego, 1996;
14. c) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287;
15. d) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, Weinheim, 1992.
16. A. Ogawa, D. P. Curran, J. Org. Chem. 1997, 62, 450-451.
17. [2] or both are the active oxidants in this reaction are underway.
18. A multistep route to this type of diene is known, however the reaction requires the presence of chlorine substituents on the aryl ring, see: H. W. Heine, B. J. Barchiesi, E. A. Williams, J. Org. Chem. 1984, 49, 2560-2565.
19. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 1029-1032; Angew. Chem. Int. Ed. 2000, 39, 1029-1032.
20. K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 1029-1032; Angew. Chem. Int. Ed. 2000, 39, 1029-1032.