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The use of chiral vinyl ethers in the cycloaddition of (E)-2- substituted and (E)-1,2-disubstituted 1-nitroalkenes is extrememly effective in providing enantiomerically enriched cycloadducts in good yield and with high diastereocontrol. For examples see footnotes 1 and 28 as well as: Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
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For total syntheses of (+)-mesembrine see: (a) Yamada, S.; Otani, G. Tetrahedron Lett. 1971, 12, 1133. (b) Kosugi, H.; Miura, Y.; Kanna, H.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1409. (c) Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
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For total syntheses of natural (-)-mesembrine see: (a) Strauss, H. F.; Weichers, A. Tetrahedron Lett. 1979, 20, 4495. (b) Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479. (c) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239. (d) Yoshimitsu, T.; Ogasawara, K. Heterocycles 1996, 42, 135.
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For total syntheses of natural (-)-mesembrine see: (a) Strauss, H. F.; Weichers, A. Tetrahedron Lett. 1979, 20, 4495. (b) Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479. (c) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239. (d) Yoshimitsu, T.; Ogasawara, K. Heterocycles 1996, 42, 135.
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84920295012
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For the preparation of nitroalkene 2 see reference 13
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For the preparation of nitroalkene 2 see reference 13.
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84920295011
-
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note
-
2, methylaluminum(bis-2,6-diisopropylphenoxide) (MAIPh), and methyl aluminum bis(2,6-diphenylphenoxide) (MAPh) were found to be ineffective in promoting the desired cycloaddition.
-
-
-
-
70
-
-
84920295010
-
-
note
-
Isomerization can also be achieved using DMAP in methylene chloride. Starting from either the pure (Z)- or (E)-nitroalkene, a mixture of nitroalkenes isomers was recovered in approximately a 5/1 (E/Z) ratio in 53% yield. The rest of the material consisted of a mixture of nitroalkenes in which the olefin had isomerized away from the nitro substituent.
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74
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84920295009
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note
-
(b) The TCC vinyl ether 16 has been found to undergo highly selective exo-mode [4 + 2] cycloadditions when using the aluminum-based Lewis acid MAPh.
-
-
-
-
75
-
-
84920295008
-
-
note
-
A racemic sample of the N-protected amine (±)-20 that was needed to establish chiral HPLC conditions was prepared from racemic vinyl ether (±)-16 using a parallel sequence of reactions.
-
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76
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37049160091
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0002455223
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38c (e) Dess-Martin periodmane: Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155
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Griffith, W.P.1
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86
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84920295007
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38c
-
38c (e) Dess-Martin periodmane: Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155
-
-
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88
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0000471319
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Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773.
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Narasaka, K.1
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89
-
-
84920295006
-
-
note
-
2O) that followed the conversion of the starting aldehyde into a single product.
-
-
-
-
90
-
-
2142787777
-
-
The alkoxymethylene group has been commonly used as a blocking group for alkylations of unsymmetrical ketones. Johnson, W. S.; Posvic, H. J. Am. Chem. Soc. 1947, 69, 1361.
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Johnson, W.S.1
Posvic, H.2
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91
-
-
84920295005
-
-
note
-
A sample of the hydrochloride salt of natural mesembrine (∼7 mg) was kindly provided by Professor Steven A. Martin (University of Texas). Conversion of the hydrochloride salt back to the free amine was accomplished by passing a chloroform solution of the sample through a short plug of basic alumina (activity I).
-
-
-
-
92
-
-
8244232809
-
-
M. Sc. Thesis, University of Pretoria
-
Nieuwenhuis, J. J. M. Sc. Thesis, University of Pretoria, 1971
-
(1971)
-
-
Nieuwenhuis, J.J.1
-
93
-
-
84920295004
-
-
note
-
13C NMR spectra of natural and synthetic mesembrine is included in the Supporting Information.
-
-
-
-
94
-
-
84920295003
-
-
Unpublished results, University of Illinois, Urbana
-
Middleton, D. S. Unpublished results, University of Illinois, Urbana.
-
-
-
Middleton, D.S.1
-
95
-
-
84920295002
-
-
The program Macromodel version 3.5a, Columbia University, was employed for these caculations
-
The program Macromodel version 3.5a, Columbia University, was employed for these caculations.
-
-
-
-
96
-
-
84920295001
-
-
rel = 0.55 kcal/ mol) exhibited very little π-facial shielding
-
rel = 0.55 kcal/ mol) exhibited very little π-facial shielding.
-
-
-
-
97
-
-
84920295000
-
-
The si- and re-faces of the enol ether are defined with respect to the C(1) alkoxy-bearing carbon atom
-
The si- and re-faces of the enol ether are defined with respect to the C(1) alkoxy-bearing carbon atom.
-
-
-
-
98
-
-
84920294999
-
-
The re- and si-faces of the nitroalkene are defined at the β-carbon atom of the nitroalkene
-
The re- and si-faces of the nitroalkene are defined at the β-carbon atom of the nitroalkene.
-
-
-
|