✍ Scribed by Corinne Fruit; Paul Müller
No coin nor oath required. For personal study only.
Dedicated to Dr. G¸nther Ohloff on the occasion of his 80th birthday Enantioselective intramolecular amidation of aliphatic sulfonamides was achieved for the first time by means of chiral carboxylatodirhodium(II) catalysts in conjunction with PhI(OAc) 2 and MgO in high yields and with enantioselectivities of up to 66% (Scheme 3, Table 1). The best results were obtained with [Rh 2 {(S)-nttl) 4 ] and [Rh 2 {(R)-ntv) 4 ] as catalysts ((S)-nttl (aS)-a-(tert-butyl)-1,3-dioxo-2H-benz[de]isoquinoline-2-acetato, (R)-nto (aR)-a-isopropyl-1,3-dioxo-2H-benz[de] isoquinoline-2-acetato). In addition, these carboxylatodirhodium(II) catalysts were also efficient in intramolecular amidations of aliphatic sulfamates esters, although the enantioselectivity of these latter reactions was significantly lower (Scheme 4, Table 3).
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