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For excellent reviews on the asymmetric Strecker synthesis see ref If-h. See also: Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179.
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2AlCN to an N-[1-(triethoxymethyl)ethylidene]sulfinamide. Hua, D. H.; Lagneau, Wang, H.; Chen, C Tetrahedron: Asymmetry 1995, 6, 349.
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85033857716
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note
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3).
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15
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85033833098
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note
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3).
-
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16
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85033834365
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note
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2AlCN as evidenced by the lack of ethane formation and the similar de's to those observed in the absence of added alcohol.
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17
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0001032785
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85033870609
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note
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Shift reagents studies with tris[3-heptafluoropropylhydroxymethylene-(+)-camphorato]europium(III) indicates that the sulfinyl oxygen is the site of greatest Lewis basicity in 1.
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20
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85033843689
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Unpublished results
-
Under similar conditions, the N-(p-nitrobenzylidene)sulfinamide 1 (R = p-nitrophenyl) fails to react within 3 h. Davis, F. A.; Portonovo, P. S; Fanelli, D. Unpublished results.
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0002256381
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Patai, S., Ed.; John Wiley: New York, Chapter 12
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For substituted aromatic aldehydes and imines, electronattracting substituents increase the rate of addition. Aliphatic aldehydes are somewhat more reactive than aromatic aldehydes because of resonance stabilization in the latter. In aliphatic aldehydes α-methyl groups reduce the reactivity toward addition of nucleophiles. For discussions of these points see: Reeves, R. L. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; John Wiley: New York, 1966; Vol. 1, Chapter 12. Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Zabicky, J., Ed.; John Wiley: New York, 1970; Vol. 2, Chapter 1.
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0003830917
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Zabicky, J., Ed.; John Wiley: New York, Chapter 1
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For substituted aromatic aldehydes and imines, electronattracting substituents increase the rate of addition. Aliphatic aldehydes are somewhat more reactive than aromatic aldehydes because of resonance stabilization in the latter. In aliphatic aldehydes α-methyl groups reduce the reactivity toward addition of nucleophiles. For discussions of these points see: Reeves, R. L. In The Chemistry of the Carbonyl Group; Patai, S., Ed.; John Wiley: New York, 1966; Vol. 1, Chapter 12. Ogata, Y.; Kawasaki, A. In The Chemistry of the Carbonyl Group; Zabicky, J., Ed.; John Wiley: New York, 1970; Vol. 2, Chapter 1.
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