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Volumn 52, Issue 15, 1987, Pages 3435-3441

Diastereoselective 1,2-Addition of Lithiated N-(TrialkylsilyOmethylphenylsulfoximines to Aldehydes: Preparation of l,4,3-Oxathiazin-2(6H)-one 4-Oxides as Novel Cyclic Sulfoximines

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EID: 0001163288     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00391a049     Document Type: Article
Times cited : (34)

References (20)
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    • High diastereoselectivity has been noted in the 1,2-addition of lithiated 2a to sterically congested cyclic ketones: (b) J. Am. Chem. Soc. 1982, 104, 4021. (c) Johnson, C. R.; Meanwell, N. J. Org. Chem. 1981, 103, 7667. For an imaginative preparation of oxetanes via 1,2-addition of the anion derived from 2b, see: Welch, S. C. Prakasa Rao, A. S. C.; Lyon, J. T.; Assercq, J. M. J. Am. Chem. Soc. 1983, 105, 252.
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    • It should be noted that the stereochernical results of metal hydride reductions of β-keto sulfoximines are ambiguous with regard to the favorability of oxygen versus nitrogen chelation: (b) Annunziata, R.; Cin-quini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. 1 1981, 1109. (c) Johnson, C. R.; Stark, C. J., Jr. Tetrahedron Lett. 1979, 4713.
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