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Synlett 1992; 1992(1): 27-30
DOI: 10.1055/s-1992-21253
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N-Nitrosulfoximines as Chemical Chameleons for Asymmetric Synthesis

Barry M. Trost* , Richard T. Matsuoka
  • *Department of Chemistry, Stanford University, Stanford, California 94305, USA
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Publication Date:
18 September 2002 (online)

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In contrast to N-tosylsulfoximines, the relatively obscure N-nitrosulfoximines show good diastereoselectivity in alkylations and extraordinarily good leaving group properties in cyclizations via SN2 displacement. Thus, methyl phenyl N-nitrosulfoximine serves as a chiral lynchpin for construction of chiral ring systems.