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Schmitt, A.1
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For recent contributions of other groups: [6e] Y. Nishiyama, T. Katoh, K. Deguchi, Y. Morimoto, K. Itoh, J. Org. Chem. 1997, 62, 9339-9341.
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(B. M. Trost, E. Winterfeldt, Eds.), Pergamon Press, Oxford chpt. 1.2
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Review: R. R. Schmidt in Comprehensive Organic Synthesis (B. M. Trost, E. Winterfeldt, Eds.), Pergamon Press, Oxford 1991, Vol. 6, chpt. 1.2.
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Schmidt, R.R.1
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For reactions of free γ-lactols see: [8a] K. Tomooka, K. Matsuzawa, K. Suzuki, G.-i. Tsuchihashi, Tetrahedron Lett. 1987, 28, 6339-6342.
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[8c] G. H. Posner, S. R. Haines, Tetrahedron Lett. 1985, 26, 1823-1826; see this ref. for reactions of activated or protected γ-lactols.
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Posner, G.H.1
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K. Hori, N. Hikage, A. Inagaki, S. Mori, K. Nomura, E. Yoshii, J. Org. Chem. 1992, 57, 2888-2902.
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0000914963
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S. Murata, M. Suzuki, R. Noyori, Tetrahedron 1988, 44, 4259-4275.
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Murata, S.1
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0006912022
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[8i] D. S. Brown, M. Bruno, R. J. Davenport, S. V. Ley, Tetrahedron 1989, 45, 4292-4308.
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0001897420
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D. S. Brown, P. Charreau, S. V. Ley, Synlett 1990, 749-750; see these refs. for related reactions of substituted 2-phenylsulfonyltetrahydrofurans.
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Synlett
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Brown, D.S.1
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39
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0001204097
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A. Schmitt, H.-U. Reißig, Synlett 1990, 40-42; see this ref. for preliminary communication of our results.
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Synlett
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Schmitt, A.1
Reißig, H.-U.2
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40
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0000840923
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[10a] G. A. Kraus, K. A. Frazier, B. D. Roth, M. J. Taschner, K. Neuenschwander, J. Org. Chem. 1981, 46, 2417-2419.
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Neuenschwander, K.5
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43
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0006909622
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note
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The corresponding cis-4,5-dimethyl-substituted γ-lactol could only be obtained as an enriched mixture with 5 as a minor component. However, its reaction with 8 in the presence of boron trifluoride is highly stereoselective, giving only the 2,4-trans-2,5-trans diastereomer (in admixture with the two isomers of 25). In this case, the two methyl groups cooperate, resulting in excellent diastereoselectivity.
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44
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33847562204
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manuscript in preparation
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A. Schmitt, H.-U. Reißig, manuscript in preparation; for the preparation of (phenylselenenyl)tetrahydrofuran derivatives see this ref.
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Schmitt, A.1
Reißig, H.-U.2
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45
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0006989349
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note
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Unfortunately, the acetates derived from γ-lactols used in this study were rather unstable. Thus, we could not investigate stereoselectivity with these substrates.
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47
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0024815564
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S. E. Denmark, T. W. Willson, N. G. Almstead, J. Am. Chem. Soc. 1989, 111, 9258-9260.
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H. Matsutani, S. Ichikawa, J. Yaruva, T. Kusumoto, T. Hiyama, J. Am. Chem. Soc. 1997, 119, 4541-4542.
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0001405730
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[16b] M. Lj. Mihailovic, R. I. Mamuzic, Lj. Zigic-Mamuzic, J. Bosniak, Z. Cekovic, Tetrahedron 1967, 23, 215-226.
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Mihailovic, M.Lj.1
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H. Angert, T. Kunz, H.-U. Reißig, Tetrahedron 1992, 48, 5681-5690.
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Angert, H.1
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Reißig, H.-U.3
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58
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33847537994
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MM2 & P1, QCPE 395 +318 (P1) program packace PCMO-DEL, Serena Software
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]19] K. E. Gilbert, J. J. Gajewski, program MMX, version 89.000, MM2 & P1, QCPE 395 +318 (P1) program packace PCMO-DEL, Serena Software.
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Program MMX, Version 89.000
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Gilbert, K.E.1
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33847547396
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G. Rauhut, A. Schmitt, unpublished ab initio 6-31G* calculations, Technische Hochschule Darmstadt, 1991
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G. Rauhut, A. Schmitt, unpublished ab initio 6-31G* calculations, Technische Hochschule Darmstadt, 1991.
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62
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1542554559
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The problem may be regarded as a Curtin-Hammett system with "feed in" mechanism, since the low activation barrier between the two conformers guarantees that their equilibrium is always established. For a discussion see: J. I. Seeman, Chem. Rev. 1983, 83, 83-134.
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Seeman, J.I.1
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For recent reactions of related disubstituted oxocarbenium ions see: [23al J. Ishihara, J. Miyakawa, T. Tsujimoto, A. Murai, Synlett 1997, 1417-1419.
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