Generation of oxyallyl cations by reduction of α,α′-diiodoketones under sonochemical or thermal conditions: Improved methodology for the [4C(4π)+3C(2π)] cycloaddition reactions

Synthetic Communications

Volumn 33, Issue 2, 2003, Pages 265-279

  Montaña, Angel M ^a   Grima, Pedro M ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALLYL COMPOUND; ALPHA,ALPHA' DIIODOKETONE; CATION; COPPER; IODINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; EDUCATION; LOW TEMPERATURE; POWDER; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS; TEMPERATURE; TEMPERATURE SENSITIVITY; ULTRASOUND;

EID: 0037272496     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015712     Document Type: Article

References (44)

1. (a) Noyori, R.; Hayakawa, Y. Reductive dehalogenation of polyhalo ketones with low-valence metals and related reducing agents. Org. react. 1983, 29, 163-343;
2. (b) Mann, J. The Synthetic utility of oxyallyl cations. Tetrahedron 1986, 42, 4611-4659;
3. (c) Hoffmann, H.M.R. The cycloaddition of allyl cations to 1,3-dienes: general method for the synthesis of seven-membered carbocycles. Angew. Chem. Int. Ed. Eng. 1984, 23, 1-88;
4. (d) Rigby, J.H.; Pigge, F.C. [4+3] Cycloaddition reactions. Org. React. 1997, 51, 351-478.
5. (a) Montaña, A.M.; Nicholas, K.M.; Khan, M.A. An approach to pseudoguaianolides via cobalt-mediated cyclopentannelation: a stereochemical aside. J. Org. Chem. 1988, 53 (22), 5193-5201;
6. (b) Montaña, A.M.; Nicholas, K.M. Cobalt-mediated synthesis of a versatile pseudoguaianolide intermediate. J. Org. Chem. 1990, 55 (5), 1569-1578.
7. (a) Montaña, A.M.; Ribes, S.; Grima, P.M.; García, F. Study of cis/trans and endo/exo diastereoselectivity in the [4+3]-cycloaddition reaction of 2-functionalized furans and dimethyloxyallyl cation. Preparation of versatile cycloheptane synthons. Chem. Lett. 1997, 9, 847-848;
8. (b) Montaña, A.M.; Ribes, S.; Grima, P.M.; García, F.; Solans, X.; Fontbardia, M. 2-Functionalized furans as precursors of versatile cycloheptane synthons. Tetrahedron 1997, 53, 11669-11684.
9. Montaña, A.M.; Ribes, S.; Grima, P.M.; García, F. α-Hetero-substituted furans as dienes in [4+3] cycloaddition with 1,3-dimethyloxyallyl cation for the preparation of new versatile cycloheptane synthons: a study of the factors controlling the diastereoselectivity. Act. Chem. Scand. 1998, 52, 453-460.
10. (a) Montaña, A.M.; García, F.; Grima, P.M. New synthetic methodology to prepare polyfunctionalized heptane building-blocks with four stereocenters: synthesis of the (±)-C17-C23 subunit of ionomycin. Tetrahedron Lett. 1999, 40, 1375-1378;
11. (b) Montaña, A.M.; García, F.; Grima, P.M. Synthesis of the C17-C23 subunit of ionomycin from C1-functionalized 8-oxabicyclo[3.2.1](oct-6-en-3-one. New synthetic methodology to prepare polyfunctionalized heptane building blocks with four stereocenters. Tetrahedron 1999, 55, 5483-5504.
12. Montaña, A.M.; Fernández, D. Enantioselective synthesis of transfused bicyclo[5.3.0]decane systems via a tandem [4+3] cycloaddition-Nicholas reaction. Tetrahedron Lett. 1999, 40, 6499-6502.
13. Montaña, A.M.; Fernández, D.; Pagès, R.; Filippou, A.C.; Kociok-Köhn, G. Enantioselective synthetic methodology to prepare transfused bicyclo[5.3.0]decane systems: an approach to the synthesis of the pseudoguaiane carbon framework. Tetrahedron 2000, 56, 425-439.
14. Takaya, H.; Makino, S.; Hayakawa, Y.; Noyori, R. Reactions of polybromo ketones with 1,3-dienes in the presence of iron carbonyls. New [4+3] cyclocoupling reaction forming 4-cycloheptenones. J. Am. Chem. Soc. 1978, 100, 1765-1777.
15. Ashcroft, M.R.; Hoffmann, H.M.R. Bicyclic ketones for tropinone synthesis: 2α,4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one. Org. Synth. 1978, 58, 17-23.
16. Shimizu, N.; Tanaka, M.; Tsuno, Y. Generation of 2-(trimethylsiloxy)allyl cations and their reactions with 1,3-dienes. Change in mechanism of [3+4] cycloaddition with solvent. J. Am. Chem. Soc. 1982, 104, 1330-1340.
17. (a) Schmid, R.; Schmid, H. Silberioneninduzierte reaktion von 3-chlor-2-pyrrolidinocyclohexen mit 1,3-dienen. Helv. Chim. Acta 1974, 57, 1883-1886;
18. (b) Oh, J.; Ziani-Cherif, C.; Choi, J.R.; Cha, J.K. [4+3] Cycloaddition of aminoallyl cations with 1,3-dienes: 11-oxatricyclo[4.3.1.1[2,5]]undec-3-en-10-one. Org. Synth. 2000, 78, 212-219.
19. De Kimpe, N.; Palamareva, M.; Verhe, R.; De Buyck, L.; Schamp, N. Silver-induced conversion of α-chloroketimines into 2-dimethyl-3-(N-alkyl)imino-8-oxabicyclo[3.2.1]oct-6-enes. J. Chem. Research (S) 1986, 190-191.
20. Hill, A.E.; Hoffmann, H.M.R. One stage synthesis of bicyclo[3.2.2]-nona-6,8-dien-3-ones. The silver trifluoroacetate induced reaction of 2-methoxyallyl bromide with arenes. J. Am. Chem. Soc. 1974, 96, 4597-4603.
21. Murray, D.H.; Albizati, K.F. Ambiphilic reactivity of 1,1-dimethoxyacetone. Tetrahedron Lett. 1990, 31, 4109-4112.
22. Hoffmann, H.M.R. Allyl alcohols as precursors of allyl cations. Chem. Ber. 1980, 113, 3837-3847.
23. Sakurai, H.; Shirahata, A.; Hosomi, A. 3-Bromo-3-methyl-2-trimethylsililoxy-1-butene. A new cycloaddition reagent. Angew. Chem., Int. Ed. Engl. 1979, 18, 163-164.
24. Harmata, M.; Elahmad, S.; Barnes, C.L. Intramolecular [4+3] cycloadditions. The synthesis of cyclooctanoids. J. Org. Chem. 1994, 59, 1241-1242.
25. Sasaki, T.; Ishibashi, Y.; Ohno, M. Catalized cycloaddition reactions of α-silyloxy α,β-unsaturated ketones and aldehydes. Tetrahedron Lett. 1982, 23, 1693-1696.
26. (a) Mann, J.; Wilde, P.D.; Finch, M.W.J. Rearrangements of aryl-8-oxabicyclo[3.2.1]octenones: synthesis of novel biaryl and 1-aryl-3-furylpropanones. Chem. Soc., Chem. Commun. 1985, 1543-1544;
27. (b) Föhlisch, B.; Gehrlach, E.; Herter, R. Efficient synthesis of 8-oxabicyclo[3.2.1]oct-6-en-3-ones, preparatively useful [4+3]-cycloadducts. Angew. Chem. Int. Ed. Engl. 1982, 2, 137;
28. (c) Herter, R.; Föhlisch, B. Lithiumperchlorat/triethylamin, ein neues reagens zur synthese von 3-oxo-8-oxabicyclo[3.2.1]oct-6-enen aus α-haloketonen und furan. Synthesis 1982, 976-979.
29. Joshi, N.N.; Hoffmann, H.M.R. Ultrasonics in the metal promoted cycloaddition of α,α-dibromoketones to 1,3-dienes. Tetrahedron Lett. 1986, 27 (6), 124-154.
30. (a) Pestman, J.M.; Engberts, J.B.F.N.; de Jong, F. Sonochemistry: theory and applications. Recl. Trav. Chim. Pays-Bas 1994, 113 (12), 533;
31. (b) Suslick, K.S. Sonochemistry. Science 1990, 247, 1439;
32. (c) Mason, T.J.; Lorimer, P.J. Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry, 1st Ed.; John Wiley: New York, 1988; 1-245;
33. (d) Mason, T.J. Chemistry with Ultrasound, 1st Ed.; Elsevier: London, 1990; 1-186.
34. (a) Einhorn, C.; Einhorn, J.; Luche, J.L. Sonochemistry: the use of ultrasonic waves in synthetic organic chemistry. Synthesis (Review) 1989, 787-810;
35. (b) Addulla, R.F. Ultrasound in organic synthesis. Aldrichimica Acta 1988, 21 (2), 31-37;
36. (c) Lindley, J.; Mason, T.J. Sonochemistry: synthetic applications. Chem. Soc. Rev. 1987, 16, 275-305;
37. (d) Boudjouk, Ph. Synthesis with ultrasonic waves. J. Chem. Educ. 1986, 63, 427-430;
38. (e) Suslick, K.S.; Doktycz, S.J. The sonochemistry of Zn powder. J. Am. Chem. Soc. 1989, 111, 2342-2348;
39. (f) Doktycz, S.J.; Suslick, K.S. Interparticle collisions driven by ultrasound. Science 1990, 247, 1067-1069.
40. Montaña, A.M.; Grima, P.M. SEM as a useful tool to evaluate the effects of ultrasound on the surface or reacting metals in cycloaddition reactions. Microscopy and Analysis 2000, 1, 9-11.
41. Smith, R.D.; Simmons, H.E. Norcarane (bicyclo[4.1.0]heptane). Org. Synth. 1961, 41, 72.
42. Montaña, A.M.; Grima, P.M. Effective, safe and inexpensive microscale ultrasonic set-up for teaching and research labs. J. Chem. Educ. 2000, 77 (6), 754-757.
43. Julian, P.L.; Karpel, W.J. The selective halogenation and dehalogenation of certain steroids. J. Am. Chem. Soc. 1950, 72, 362-366.
44. 4-3-ketosteroids. J. Am. Chem. Soc. 1950, 72, 4077-4080.