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2004
Ring closure reactions
O 0130
Intramolecular Asymmetric Amidations of Sulfonamides and Sulfamates Cataby Chiral Dirhodium(II) Complexes. — The first asymmetric intramolecular
47- 033 lyzed
amidation reaction of sulfonamides and sulfamates is presented. Aliphatic as well as
aromatic sulfonamides and sulfamates are transformed in situ to the corresponding phenyliodonium ylides and subsequently cyclized in the presence of chiral rhodium catalysts to give sultams (II), (IV), (VII) as well as cyclic sulfamidates (IX) and (XI). Best
results are achieved with the complex Rh2((S)-NTTL)4 (up to 66% e.e.). — (FRUIT*,
C.; MUELLER, P.; Helv. Chim. Acta 87 (2004) 7, 1607-1615; Dep. Org. Chem.,
Univ. Geneva, CH-1211 Geneva 4, Switz.; Eng.) — Mischke
2004
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