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For kinetic resolution through the enzymatic transesterification of racemic 3 or the hydrolysis of the corresponding esters, see: a) A. J. M. Janssen, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 1991, 47, 7645-7662; b) J. Kaminska, I. Górnicka, M. Sikora, J. Góra, Tetrahedron: Asymmetry 1996, 7, 907-910.
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49
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0000973754
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During the intramolecular Diels-Alder reaction of furans, the equilibrium of the cycloadducts and their precursors has often been observed, see: a) C. Rogers, B. A. Keay, Can. J. Chem. 1993, 71, 611-622; b) N. Iwasawa, F. Sakurada, M. Iwamoto. Org. Lett. 2000, 2, 871-873.
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Rogers, C.1
Keay, B.A.2
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50
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0000728738
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During the intramolecular Diels-Alder reaction of furans, the equilibrium of the cycloadducts and their precursors has often been observed, see: a) C. Rogers, B. A. Keay, Can. J. Chem. 1993, 71, 611-622; b) N. Iwasawa, F. Sakurada, M. Iwamoto. Org. Lett. 2000, 2, 871-873.
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Iwasawa, N.1
Sakurada, F.2
Iwamoto, M.3
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51
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2142782962
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note
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[10] were erroneously drawn and need to be corrected. The revised structures are shown in Scheme 4.
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52
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2142670716
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note
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2 at 30°C for 4-6 days. In several repeated trials, optically enriched products, -4a (7-9% ee), (2R)-syn-5a (0-8% ee), and (2R)-anti-5a (0-23% ee) were obtained; however, the degree of the optical purity was small and varied. Further investigation is now being continued.
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53
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2142849977
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note
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[12a]
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K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467-4470; H. Mosimann, P. Vogel, J. Org. Chem. 1997, 62, 3002-3007.
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0037016980
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For synthetic studies, see: D. L. Wright, C. V. Robotham, K. Aboud, Tetrahedron Lett. 2002, 43, 943-946; F. E. S. Souza, R. Rodrigo, Chem. Commun. 1999, 1947-1948.
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Souza, F.E.S.1
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0033597147
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For total synthesis, see: M. Takadoi, T. Katoh, A. Ishiwata, S. Terashima, Tetrahedron Lett. 1999, 40, 3399-3402; S. Chackalamannil, R. J. Davies, Y. Wang, T. Asberom, D. Doller, J. Wong, D. Leone, A. T. McPhail, J. Org. Chem. 1999, 64, 1932-1940.
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For total synthesis, see: M. Takadoi, T. Katoh, A. Ishiwata, S. Terashima, Tetrahedron Lett. 1999, 40, 3399-3402; S. Chackalamannil, R. J. Davies, Y. Wang, T. Asberom, D. Doller, J. Wong, D. Leone, A. T. McPhail, J. Org. Chem. 1999, 64, 1932-1940.
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Wong, J.6
Leone, D.7
McPhail, A.T.8
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62
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note
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Quite recently, we developed a new domino process involving a lipase-catalyzed kinetic resolution of hydroxy nitrons followed by the intramolecular [3 + 2] polar cycloaddition, which will be reported in the near future.
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For reviews, see: S. Laschat, Angew. Chem. 1996, 108, 313-315; Angew. Chem. Int. Ed. Engl. 1996, 35, 289-291; A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394; G. Pohnert Chem BioChem 2001, 2, 873-875; see also: K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas. J. Am. Chem. Soc. 2000,. 122, 11519-11520.
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75
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2142835967
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note
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6]acetone.
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