A highly diastereoselective [2,3]-sigmatropic N,O rearrangement

Chemical Communications

Volumn , Issue 20, 1999, Pages 2079-2080

  Bull, Steven D ^a   Davies, Stephen G ^a   Jones, Simon ^a   Ouzman, Jacqueline V A ^a   Price, Anne J ^a   Watkin, David J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; LITHIUM N BENZYL O (4 METHOXY 4 PHENYLBUT 2 ENYL)HYDROXYLAMIDE; SYN 3 BENZYLAMINO 4 METHOXY 4 PHENYLBUT 1 ENE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL STRUCTURE; DIASTEREOISOMER;

EID: 0033592720     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905981d     Document Type: Article

References (11)

1. S. M. Roberts, in Comprehensive Functional Group Transformations, ed. A. R. Katritzky, O. Meth-Cohn and C.W. Rees, Pergamon, Oxford, 1995, vol. 1, p. 404.
2. S. G. Davies, S. Jones, M. A. Sanz, F. C. Teixeira and J. F. Fox, Chem. Commun., 1998, 2235.
3. Y. D. Wu, K. N. Houk and J. A. Marshall, J. Org. Chem., 1990, 55, 1421.
4. For examples of the synthetic utility of the [2,3]-Wittig rearrangement, see T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885; 'The Wittig Rearrangement' in C-C σ Bond Formation, ed. G. Pattenden, vol. 3 of Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1990, p. 975.
5. For examples of the synthetic utility of the [2,3]-Wittig rearrangement, see T. Nakai and K. Mikami, Chem. Rev., 1986, 86, 885; 'The Wittig Rearrangement' in C-C σ Bond Formation, ed. G. Pattenden, vol. 3 of Comprehensive Organic Synthesis ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1990, p. 975.
6. K. Mikami and T. Nakai, Synthesis, 1991, 594; R. Brückner and H. Pnepke, Angew. Chem., 1988, 27, 278; H. Priepke and R. Brückner, Chem. Ber., 1990, 123, 153.
7. K. Mikami and T. Nakai, Synthesis, 1991, 594; R. Brückner and H. Pnepke, Angew. Chem., 1988, 27, 278; H. Priepke and R. Brückner, Chem. Ber., 1990, 123, 153.
8. K. Mikami and T. Nakai, Synthesis, 1991, 594; R. Brückner and H. Pnepke, Angew. Chem., 1988, 27, 278; H. Priepke and R. Brückner, Chem. Ber., 1990, 123, 153.
9. R. Brückner, Chem. Ber., 1989, 122, 193; E. Nakai and T. Nakai, Tetrahedron Lett., 1988, 29, 4587.
10. R. Brückner, Chem. Ber., 1989, 122, 193; E. Nakai and T. Nakai, Tetrahedron Lett., 1988, 29, 4587.
11. For an example where the diastereoselectivity observed fora [2,3]-Wittig rearrangement has been rationalised via a chelated transition state, see S. W. Scheuplein, A. Kusche, R. Brückner and K. Harms, Chem. Ber., 1990, 123, 917.