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Desymmetrization of meso-N-Sulfonylaziridines with Chiral Nonracemic Nucleophiles and Bases

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Published in Helvetica chimica acta. 2001, vol. 84, no. 3, p. 662-677
Abstract The cyclohexene‐derived aziridine 7‐tosyl‐7‐azabicyclo[4.1.0]heptane (1) reacts with Grignard reagents in the presence of chiral nonracemic Cu‐catalysts to afford sulfonamides 3a – e (Scheme 3) in up to 91% ee under optimized conditions (Table 2). No activation of the aziridine by Lewis acids is required. The reaction may be extended to other bicyclic N‐sulfonylated aziridines, but aziridines derived from acyclic olefins, cyclooctene, and trinorbornene are unreactive under standard conditions (Scheme 5). Exposure of 1 to s‐BuLi in the presence of (−)‐sparteine (2.8 equiv.) affords the allylic sulfonamide 31 in 35% yield and 39% ee (Scheme 6). Under the same conditions, the aziridines 33 and 35 yield products 34 and 36 derived from intramolecular carbenoid insertion with 75 and 43% ee, respectively.
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MULLER, Paul, NURY, Patrice. Desymmetrization of meso-N-Sulfonylaziridines with Chiral Nonracemic Nucleophiles and Bases. In: Helvetica Chimica Acta, 2001, vol. 84, n° 3, p. 662-677. doi: 10.1002/1522-2675(20010321)84:3<662::AID-HLCA662>3.0.CO;2-P https://archive-ouverte.unige.ch/unige:119361

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Deposited on : 2019-06-13

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