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Volumn 71, Issue 11, 2006, Pages 4270-4279

Palladium-catalyzed intramolecular asymmetric hydroamination, hydroalkoxylation, and hydrocarbonation of alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINATION; BENZENE; CATALYST ACTIVITY; PALLADIUM; PROBABILITY DENSITY FUNCTION; REACTION KINETICS; STEREOCHEMISTRY;

EID: 33646934925     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0603835     Document Type: Article
Times cited : (147)

References (128)
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    • note
    • Intramolecular asymmetric hydroalkoxylation and hydrocarbonation are not known in the literature. For asymmetric intramolecular hydroamination, see refs 15 and 16.
  • 55
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    • Enhancement of reaction rate by the use of the Pd(0)/carboxylic acid combined catalytic system is also observed by others. See: (a) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161-3163.
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    • For a review, see: (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412.
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    • This process is similar to the hydroacylation process for the allylation of acetic acid with alkynes which gives allylic acetates. See: Trost, B. M.; Brieden, W.; Baringhaus, K. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 1335-1336.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1335-1336
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    • Ref 10d
    • (e) Ref 10d.
  • 76
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    • Recently, Kim and Livinghouse reported enantioselective intramolecular hydroamination of alkene with ee's ranging from 69% to 89%. See: (i) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
    • (2005) Org. Lett. , vol.7 , pp. 1737-1739
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    • Ref 15c
    • (f) Ref 15c.
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    • note
    • The formation of the chiral rhodium complex Rh(I)-renorphos is known; see ref 32. However the formation of the Pd-renorphos complex has not been known in the literature.
  • 86
    • 33646914752 scopus 로고    scopus 로고
    • note
    • See the Supporting Information for details.
  • 87
    • 13244289964 scopus 로고    scopus 로고
    • There are innumerable reports on the synthesis and importance of optically active cyclic ethers. For instance, see: (a) Pohlhaus, P. D.; Johnson. J. S. J. Org. Chem. 2005, 70, 1057-1059.
    • (2005) J. Org. Chem. , vol.70 , pp. 1057-1059
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    • note
    • Efforts to determine the ee of 10e were undertaken using GC with different chiral columns. However, no satisfactory separation of enantiomers could be obtained.
  • 93
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    • note
    • We tested the reactivity of the following substrates. Unlike the hydrocarbonation, these substrates proved inert under conditions A and B. (Diagram presented)
  • 94
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    • 2Ph and COOEt, instead of CN) at the end of the tethered carbon chain; however, the desired products were not obtained at all; instead, the corresponding dienes were obtained. For the formation of 1,3-dienes from π-allyl-Pd species, see: (a) Takacs, J. M.; Lawson, E. C.; Clement, F. J. Am. Chem. Soc. 1997, 117, 55956-5957.
    • (1997) J. Am. Chem. Soc. , vol.117 , pp. 55956-55957
    • Takacs, J.M.1    Lawson, E.C.2    Clement, F.3
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    • Palladium-catalyzed isomerization of alkynes to allenes, see: (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1986, 27, 4893-4894.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4893-4894
    • Sheng, H.1    Lin, S.2    Huang, Y.3
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    • note
    • (c) See refs 24a and 24b.
  • 101
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    • The theoretical data on the Pd-catalyzed enantioselective reactions is rather limited, see: (a) Tang, D.; Luo, X.; Shen, W.; Li, M. J. Mol. Struct.: THEOCHEM 2005, 716, 79-87.
    • (2005) J. Mol. Struct.: THEOCHEM , vol.716 , pp. 79-87
    • Tang, D.1    Luo, X.2    Shen, W.3    Li, M.4
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    • Before the recent DFT study of asymmetric allylic alkylation only the mechanism of the epimerization of π-allyl-Pd intermediates was studied, see: (b) Sakaki, S.; Nishikawa, M.; Ohyoshi, A.; J. Am. Chem. Soc. 1980, 102, 4062-4069.
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    • note
    • The -Ts protecting group was used because the determination of the ee of the product from the corresponding Nf-protected compound proved difficult.
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    • 3), 94% ee}. For the preparation of chiral allene from chiral propynyl methanesufonates, see: Elsevier, C. J.; Vermeer, P. J. Org. Chem. 1989, 54, 3726-3730.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.