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9244236282
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note
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d) N-(diazoacetyl)oxazolidinone 1d can be easily prepared from the reaction of (S)-(-)-4-benzyl-2-oxazolidinone with triphosgene, followed by treatment with diazomethane, or by deprotonation of (5)-(-)-4-benzyl-2- oxazolidinone acetamide with LDA and diazo transfer from o-nitrophenylsulfonyl azide. See the Supporting Information for details.
-
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-
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38
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0039255361
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and references therein
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The use of HMPA for improving the diastereoselectivity in lithium enolate reactions has been reported; see: E. Juaristi, J. L. León-Romo, Y. Ramírez-Quirós, J. Org. Chem. 1999, 64, 2914, and references therein.
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9244247039
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note
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a) CCDC-239004 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk);
-
-
-
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40
-
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9244221354
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-
note
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b) the R configuration was also confirmed by correlating the product 3da with the known compound (2R,3S)-11a. See the Supporting Information.
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41
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0001128104
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44
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9244233083
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note
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Although the exact structure of the deprotonated diazoacetyl compound is not known, it should be more reasonable to consider it as a carbanion, in which the negative charge is localized on the diazo-bound carbon atom.
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45
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9244256493
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ref. [9,10]
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HMPA has been known to dramatically alter the regio- and/or stereoselectivity in the reaction of lithium enolates with electrophiles; see a) ref. [9,10];
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49
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0342713705
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Chelated and nonchelated enolates derived from Evans' reagents have been reported to give opposite stereoselectivities in aldol reactions, see: M. A. Walker, C. H. Heathcock, J. Org. Chem. 1991, 56, 5747.
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9244264179
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note
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2O, were also examined, but the diazo compound 3a decomposes to give a complex mixture of products.
-
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54
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-
9244265805
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-
note
-
1H NMR (400 MHz) spectrum of the crude product of each reaction.
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55
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0344153836
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4 has been reported: J.-M. Lee, H.-S. Lim, K.-C. Seo, S.-K. Chung, Tetrahedron: Asymmetry 2003, 14, 3639;
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56
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9244241768
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unpublished results
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b) the assignment of the relative stereochemistry is based on the correlation of the product 11a with the known compound (2A,3S)-11a, and an X-ray crystal structure of the reduction product of the racemic α-keto β-amino ester: Y. Zhao, N. Jiang, S. Zhang, J. Wang, unpublished results.
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Zhao, Y.1
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