Facial selectivity in the reactions of 1,3-dipoles with cis- and trans-3,4-dimethyl-1-methoxycarbonyl cyclobutenes

Tetrahedron

Volumn 53, Issue 27, 1997, Pages 9279-9292

  Cinquini, Enrico ^a   Freccero, Mauro ^a   Gandolfi, Remo ^a   Amade', Mirko Sarzi ^a   Rastelli, Augusto ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; CONFORMATION; DIASTEREOISOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031008036     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00539-5     Document Type: Article

References (24)

1. Burdisso, M.; Gandolfi, R.; Lucchi, M.; Rastelli, A. J. Org. Chem. 1990, 55, 2123-2125.
2. Rastelli, A.; Burdisso, M.; Gandolfi, R. J. Phys. Org. Chem. 1990, 3, 159-173.
3. Burdisso, M.; Gamba, A.; Gandolfi, R.; Toma, L.; Rastelli, A.; Schiatti, E. J. Org. Chem. 1990, 55, 3311-3321 and references cited therein.
4. Rastelli, M.; Bagatti, M.; Gandolfi, R. J.C.S. Faraday Trans. 1993, 83, 3913-3920 and references cited therein.
5. Throughout we will use the syn (anti) descriptor for attack on the double bond of 1-3 on the same (opposite) side of the allylic substituents. The same descriptors are used for out-of-plane bending , i.e., in syn (anti) bent cyclobutenes the olefinic hydrogen(s) and the COOMe group bend toward (away from) the substituents and the bending angle a is given plus (minus) sign. Anti bending of the olefinic hydrogens means also syn pyramidalization of the carbon atoms of the double bond. In the case of the trans derivative 4, in syn (anti) attacks the "C" end, i.e. the sterically more demanding end, of the 1,3-dipole is on the same (opposite) side of its vicinal methyl group, i.e. Me-6.
6. Adam, W.; Beinhauer, A.; De Lucchi, O.; Rosenthal, R. J. Tetrahedron Lett. 1983, 24, 5727-5730; Christl, M.; Mattauch, B. Chem. Ber. 1985, 118, 4203-4223.
7. Adam, W.; Beinhauer, A.; De Lucchi, O.; Rosenthal, R. J. Tetrahedron Lett. 1983, 24, 5727-5730; Christl, M.; Mattauch, B. Chem. Ber. 1985, 118, 4203-4223.
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10. Burdisso, M.; Gandolfi, R.; Pevarello, P.; Rastelli, A. J. C. S. Perkin II 1988, 753-758.
11. For previous data and discussion on coupling constants involving protons of a cyclobutane ring fused to five membered heterocyclic rings see Mondelli, R.; Gamba, A. Tetrahedron Lett. 1971, 2133-2136 and Org. Magn. Res. 1973, 5, 101-111.
12. For previous data and discussion on coupling constants involving protons of a cyclobutane ring fused to five membered heterocyclic rings see Mondelli, R.; Gamba, A. Tetrahedron Lett. 1971, 2133-2136 and Org. Magn. Res. 1973, 5, 101-111.
13. For the kinetically controlled reaction in benzene/cyclohexane (1:1) at room temperature. This ratio refers to the 4-COOMe-isoxazolidine and 5-COOMe-isoxazolidine with the same stereochemistry (i.e., with the COOMe group and the bicyclic residue of the former 6 cis to each other) as that of 14b (15b) and 16b (17b), respectively. Actually, all the possible four isomers were present in the reaction of 6 with methyl acrylate [4-COOMe (with H-3 and H-4 cis to each other)/4-COOMe (with H-3 and H-4 trans to each other)/5-COOMe (with H-3 and H-5 cis to each other)/5-COOMe (with H-3 and H-5 trans to each other) = 51.5:12:12.5:24]. Huisgen et al. have reported formation of a 5-COOR-isoxazolidine as the only product in the reaction of 6 with ethyl acrylate and methyl acrylate (Huisgen, R.; Hauck, H.; Grashey, R.; Seidl, H. Chem. Ber. 1968, 101, 2568-2584). However, we did not manage to reproduce this result and a mixture of four isomers were obtained under all the conditions [in benzene, in benzene/cyclohexane, in acetonitrile, in methyl acrylate as solvent at r.t.; yields ≥ 86%] investigated by us. Under thermodynamic control [3 days at 100 °C in benzene/methyl acrylate (1:1)] a mixture of three adducts (the 4-COOMe-isoxazolidine with H-3 and H-4 cis to each other, dominant under kinetic control, was missing) was obtained (Gandolfi, R. unpublished results).
14. Only anti adducts were obtained in the reaction of N-t-butyl nitrone with 1b, 2b and 3b, respectively, as mixtures of regioisomers (79:21, 70:30 and 73:27, respectively) in which the regioisomer with the methoxycarbonyl group at position 5 of the isoxazolidine ring (position 1 of the fused system) was dominant. In the reaction of this nitrone with methyl acrylate only the 5-substituted isoxazolidine was detected: Houk, K. N.; Bimanand, A.; Mukherjee, D.; Joyner, S.; Chang, Y. M.; Kaufman, D. C.; Domelsmith, L. N. Heterocycles, 1977, 7, 293-299. We have confirmed this observation.
15. Rastelli, A.; Gandolfi, R. submitted for publication.
16. In other words, TS geometry lessens and, respectively, increases the difference in size, between the C end and the X end of the 1,3-dipole, felt by the methyl groups in the reaction of 6 and, respectively, of 5.
17. Gandolfi, R.; Tonoletti, G.; Rastelli, A.; Bagatti, M J. Org. Chem. 1993, 58, 6038-6048 and references cited therein.
18. Sustmann, R.; Sicking, W.; Huisgen, R. J. Am. Chem. Soc., 1995, 117, 9675-9685.
19. When electrostatic interactions are important the replacement of a hydrogen atom with a COOMe group on a double bond gives rise to a significant change in face selectivity of its reactions with 1,3-dipoles: Gandolfi, R.; Sarzi Amade', M.; Rastelli, A.; Bagatti, M.; Montanari, D. Tetrahedron Lett. 1996, 37, 517-520.
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