Pelletier S.W. (Ed), Pergamon, New York, NY pp 113, 163
Anthoni U., Christophersen C., and Nielsen P.H. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives (1999), Pergamon, New York, NY pp 113, 163
Such an approach involving a Claisen rearrangement of an oxindole derivative for syntheses of (-)-flustramines and (-)-flustramides has been reported, see:
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Kawasaki T., Shinada M., Kamimura D., Ohzono M., and Ogawa A. Chem. Commun. (2006) 420
Interestingly exposure of 21b to a solution of NaOMe/MeOH (2 M, 6.10 mmol) containing hydrazine (0.51 mmol) for a day, at rt, also gave 30b in a comparable yield (39%).
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2 as the solvent, the ion pair is likely to have more covalent character. If some electrostatic attraction between the bulky cation and the ester group is invoked (Fig. 3), then the β-face becomes more shielded and diastereoselection during alkylation becomes possible. Such an attraction, among other factors, is believed to be important in explaining the origin of the enantioselectivity in the alkylation of prochiral ketones catalysed by chiral quaternary salts of Cinchona alkaloids. For the mechanism of chiral induction, see:. Ojima I. (Ed), Wiley-VCH, New York, NY pp 585, 736
2 as the solvent, the ion pair is likely to have more covalent character. If some electrostatic attraction between the bulky cation and the ester group is invoked (Fig. 3), then the β-face becomes more shielded and diastereoselection during alkylation becomes possible. Such an attraction, among other factors, is believed to be important in explaining the origin of the enantioselectivity in the alkylation of prochiral ketones catalysed by chiral quaternary salts of Cinchona alkaloids. For the mechanism of chiral induction, see:. In: Ojima I. (Ed). Chiral Asymmetric Synthesis (2000), Wiley-VCH, New York, NY pp 585, 736