Kinetic resolutions of indolines by a nonenzymatic acylation catalyst
- PMID: 17076493
- PMCID: PMC2569996
- DOI: 10.1021/ja0657859
Kinetic resolutions of indolines by a nonenzymatic acylation catalyst
Abstract
The first method for the kinetic resolution of indolines through catalytic N-acylation is described. To improve the selectivity factor, new planar-chiral PPY-derived catalysts were synthesized, wherein the chiral environment was systematically modified. This work provides a rare example of a nonenzyme-based acylation catalyst for the kinetic resolution of amines.
References
-
-
For example, see: Gueritte F, Fahy J. In: Anticancer Agents from Natural Products. Cragg GM, Kingston DGI, Newman DJ, editors. CRC Press; Boca Raton, Florida: 2005. pp. 123–135.
-
-
-
For leading references to drug candidates that bear a 2-methylindoline subunit, see: Nicolaou KC, Roecker AJ, Pfefferkorn JA, Cao G-Q. J. Am. Chem. Soc. 2000;122:2966–2967.
-
-
-
(a) For example, see: Ruthenium catalyzed hydrogenation of N-protected indoles: Kuwano R, Sato K, Kurokawa T, Karube D, Ito Y. J. Am. Chem. Soc. 2000;122:7614–7615. Kuwano R, Kashiwabara M, Sato K, Ito T, Kaneda K, Ito Y. Tetrahedron: Asymmetry. 2006;17:521–535. Kuwano R, Kashiwabara M. Org. Lett. 2006;8:2653–2655. (b) Palladium-catalyzed cyclization of N-acyl anilines: Yip K-T, Yang M, Law K-L, Zhu N-Y, Yang D. J. Am. Chem. Soc. 2006;128:3130–3131. (c) Enzyme-catalyzed hydrolysis of racemic N-Boc-indoline-2-carboxylic esters: Kurokawa M, Sugai T. Bull. Chem. Soc. Jpn. 2004;77:1021–1025.
-
-
-
(a) For reviews, see: Kagan HB, Fiaud JC. Top. Stereochem. 1988;18:249–330. Keith JM, Larrow JF, Jacobsen EN. Adv. Synth. Catal. 2001;1:5–26. Robinson DEJE, Bull SD. Tetrahedron: Asymmetry. 2003;14:1407–1446. Vedejs E, Jure M. Angew. Chem. Int. Ed. 2005;44:3974–4001.
-
-
-
For examples and leading references, see: van Rantwijk F, Sheldon RA. Tetrahedron. 2004;60:501–519.
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