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3 to the nitrogen atom of the oxazaborolidine serves to increase the Lewis acidity of the endocyclic boron atom strongly. For recent reviews, see: a) E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118; Angew. Chem. Int. Ed. 1998, 37, 1986-2012;
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2) resulted in either poor reactivity or lower enantioselectivity.
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50
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16244408273
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For other highly enantioselective Diels-Alder reactions with less than 1 mol% of chiral Lewis acid catalyst for the same substrates, see: a) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1998, 120, 8271-8272;
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b) ref. [4c].
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16244384447
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note
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4 without dramatic loss of enantioselectivity.
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53
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0029892759
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The physical and spectroscopic data for all cycloadducts were identical to those reported previously for these compounds. 2a: a) Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 118, 5502-5503;
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[4b] were assigned by comparison with optical rotation values reported in the literature. For 2b, the absolute configuration was assigned by comparison with an authentic sample prepared separately, see a) D. Sartor, J. Saffrich, G. Helmchen, Synlett 1990, 197-198.
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2b: ref. [5d]; for 2c-f, see Supporting Information; 3a: ref. [5d]; 4a: refs. [5d] and [16b]
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