Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular Heck reactions

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6261-6271

  Dounay, Amy B ^a   Hatanaka, Keiko ^a,b   Kodanko, Jeremy J ^a   Oestreich, Martin ^a,c   Overman, Larry E ^a   Pfeifer, Lance A ^a,d   Weiss, Matthew M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ASTELLAS PHARMA INC   (Japan)

^c UNIVERSITY OF FREIBURG   (Germany)

^d ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; PALLADIUM; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

HECK CYCLIZATION;

ORGANIC COMPOUNDS;

2' TRIFLATO 2 STANNYL 2 BUTENANILIDE; ANILIDE; BENZENE DERIVATIVE; CARBON; IODIDE; OXINDOLE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; HECK REACTION; ISOMERISM; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS;

CATALYSIS; CYCLIZATION; HYDROCARBONS, AROMATIC; INDOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0038287938     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034525d     Document Type: Article

References (59)

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31. Iodides that are not available from commercial sources were prepared by literature procedures or are reported in the Supporting Information: (a) Table 1, entry 6: Olah, G. A.; Lin, H. C. J. Am. Chem. Soc, 1974, 96, 2892-2898. (b) Table 1, entry 8: Witulski, B.; Buschmann, N.; Bergsträsser, U. Tetrahedron 2000, 56, 8473-8480. (c) Table 1, entry 9: Kelly, T. A.; McNeil, D. W. Tetrahedron Lett. 1994, 35, 9003-9006. (d) Table 1, entry 10: Park, Y.; Lee, I.; Kim, Y. J. Heterocycl. Chem. 1994, 31, 1625-1630.
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33. 1H NMR spectra: in all cases only two singlets were observed.
34. Other propargyl ethers were surveyed including triisopropylsilyl (TIPS) and methoxymethyl ether (MOM) derivatives. The enantiopurity of -13 prepared from these precursors was 20-30% lower than that obtained from methyl ether congener 10.
35. A Daicel Chiralcel OJ column (7:3 hexane-i-PrOH) provided baseline resolution of enantiomers; chromatograms are provided in the Supporting Information.
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37. 2 are required because 1 equiv of the diphosphine is consumed in the reduction of Pd(II to Pd(0), see: (a) Amatore, C.; Jutand, A.; Thuilliez, A. Organometallics 2001, 20, 3241-3249. (b) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
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44. See Supporting Information for details of the structural assignments for 26b, 27b. and 28b.
45. 8-THF.; complete conversion to quinolone 28b was observed within 1 h.
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47. 5c
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49. 5b.c
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55. The N-benzylacetamide substituent is undoubtedly canted nearly perpendicular to the arene in both amide rotamers of 22. This orientation is likely responsible for the observation that enantioselection is essentially the same in the cyclization of both amide rotamers.
56. The alkene and oxindole C2 substituent are perpendicular in the solid state conformation of 11k.
57. Such an orientation of the N-benzylacetamide group is observed in the X-ray structure of oxindole Heck product 23; see Figure 3.
58. General experimental details have been described: Minor, K. P.; Overman, L. E. J. Org. Chem. 1997, 62, 6379-6387.
59. Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-200985 (20), CCDC-200986 (28a), CCDC-200987 (23), CCDC-200988 (11k), and CCDC-200989 (21). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail deposit@ccdc.cam.ac.uk.).