Stereochemical aspects of intramolecular palladium catalysed [3+2] cycloadditions of methylenecyclopropanes

Tetrahedron

Volumn 52, Issue 13, 1996, Pages 4883-4902

  Corlay, Hervé ^a   Motherwell, William B ^a,c   Pennell, Andrew M K ^a   Shipman, Michael ^a,d   Slawin, Alexandra M Z ^a,d   Williams, David J ^a   Binger, Paul ^b   Stepp, Michael ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

^d LOUGHBOROUGH UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTANE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030012294     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00160-3     Document Type: Article

References (24)

1. For a comprehensive review on the intermolecular reaction, see Binger, P.; Buch, H.M.; Top. Curr. Chem., 1987, 135, 11.
2. (a) Lewis, R.T.; Motherwell, W.B.; Shipman, M.; J. Chem. Soc. Chem. Commun., 1988, 948;
3. (b) Bapuji, S.A.; Motherwell, W.B.; Shipman, M.; Tetrahedron Lett., 1989, 30, 7107;
4. (c) Motherwell, W.B.; Shipman, M.; Tetrahedron Lett., 1991, 32, 1103;
5. (d) Lewis, R.T., Motherwell, W.B.; Shipman, M.; Slawin, A.M.Z.; Williams, D.J.; Tetrahedron, 1995, 51, 3289;
6. (e) Corlay, H.; Lewis, R.T.; Motherwell, W.B.; Shipman, M.; Tetrahedron, 1995, 51, 3303.
7. (a) Yamago, S.; Nakamura, E.; J. Chem. Soc. Chem. Commun., 1988, 1112;
8. (b) Yamago, S.; Nakamura, E.; Tetrahedron, 1989, 45, 2887;
9. (c) Lautens, M. Ren, Y.; Delanghe, P.H.M.; J. Am. Chem. Soc., 1994, 116, 8821;
10. Rossi, R.; Carpita, A.; Synthesis, 1977, 561.
11. Craig, D.; Chem. Soc. Rev., 1987, 16, 187.
12. Corey, E.J.; Enders, D.; Chem. Ber., 1978, 111, 1337.
13. Corey, E.J.; Enders, D.; Tetrahedron Lett., 1976, 17, 3.
14. Blanchette, M.A.; Choy, W.; Davis, J.T.; Essenfeld, A.P.; Masamune, S.; Roush, W.R.; Sakai, T.; Tetrahedron Lett., 1984, 25, 2183.
15. Still, W.C.; Gennari, C.; Tetrahedron Lett., 1983, 24, 4405.
16. (Z)-4-(tert-Butyldiphenylsilyloxy)-2-butenal was prepared by monoprotection of commercially available cis butene-1,4-diol with tert-butyldiphenylsilyl chloride and subsequent oxidation with manganese dioxide. (E)-4-(tert-Butyldiphenylsilyloxy)-2-butenal was prepared by reduction of dimethyl fumarate with DIBAL, monoprotection of the resulting diol with tert-butyldiphenylsilyl chloride followed by oxidation with manganese dioxide (see Experimental Section).
17. Kraus, G.A.; Taschner, M.J.; J. Org. Chem., 1980, 45, 1175.
18. Neises, B.; Steglich, W.; Angew. Chem., Int. Ed. Engt., 1978, 17, 522.
19. Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1932, 51, 294; Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1934, 55, 525; Backer, H.J.; Strating, J.; Recl. Trav. Chim., 1935, 54, 170.
20. Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1932, 51, 294; Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1934, 55, 525; Backer, H.J.; Strating, J.; Recl. Trav. Chim., 1935, 54, 170.
21. Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1932, 51, 294; Backer, H.J.; Bottema, J.A.; Recl. Trav. Chim., 1934, 55, 525; Backer, H.J.; Strating, J.; Recl. Trav. Chim., 1935, 54, 170.
22. 2 of C-5 suggesting the E geometry of this double bond. All other nOe measurements were consistent with this assignment.
23. 3, o-xylene). Using this procedure, methylenecyclopropane 34 furnished the corresponding bicyclo[3.3.0]octane 35 in 30% yield. An additional product, tentatively assigned as the cyclopentene 36 (21%) was isolated from the reaction mixture. Cyclisation of homologue 37 furnished the corresponding bicyclo[4.3.0]nonane 38 in 87% yield as a 65:35 mixture of two stereoisomers. Unfortunately, exhaustive NMR studies failed to unambiguously establish the relative stereochemical relationships within the bicycles 35 and 38. Formula presented.
24. Dötz, K.H.; Popall, M.; Tetrahedron, 1985, 41, 5797.