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2005
C-C bond formation
O 0282
Self-Condensation of N-tert-Butanesulfinyl Aldimines: Application to the Rapid
Synthesis of Biologically Important Amine-Containing Compounds.
04- 056 Asymmetric
— The title reactions reported are the first examples of stereoselective imine self-condensation processes and provide versatile, functionalized intermediates with multiple
stereocenters. The diastereoselective intra- and intermolecular self-condensation reactions are applied to the total syntheses of β-amino acid (IV) and serotonin 5-HT4
agonist (X). Both syntheses feature a novel microwave-assisted thermal decomposition
to cleanly convert N-sulfinyl imines to nitriles. — (SCHENKEL, L. B.; ELLMAN*, J.
A.; Org. Lett. 6 (2004) 20, 3621-3624; Cent. New Direct. Org. Synth., Dep. Chem.,
Univ. Calif., Berkeley, CA 94720, USA; Eng.) — Steudel
2005
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