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Volumn 121, Issue 30, 1999, Pages 7026-7033

An intramolecular titanium-catalyzed asymmetric Pauson-Khand type reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CYCLOPENTENE DERIVATIVE; ENYNE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033523215     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990683m     Document Type: Article
Times cited : (139)

References (99)
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    • note
    • While the term "Pauson - Khand reaction" applies, strictly speaking, only to Co-mediated process, the term "Pauson - Khand type reaction" refers to any analogous reaction mediated or catalyzed by a transition metal.
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    • For the application of this method of absolute configuration determination to transition metal mediated carbocyclizations, see: (a) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295. (b) Reference 27. (c) Reference 28.
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    • For the application of this method of absolute configuration determination to transition metal mediated carbocyclizations, see: (a) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295. (b) Reference 27. (c) Reference 28.
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    • For the application of this method of absolute configuration determination to transition metal mediated carbocyclizations, see: (a) Urabe, H.; Takeda, T.; Hideura, D.; Sato, F. J. Am. Chem. Soc. 1997, 119, 11295. (b) Reference 27. (c) Reference 28.
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    • note
    • The metallacyclopentene derived from the enyne in entry 10 was prepared and identified in an NMR tube reaction. The use of excess enyne was necessary to ensure clean and efficient metallacycle formation. Therefore, it is difficult to assign all the peaks for the metallacycle, but its presence and diastereomeric purity are clearly indicated by a single set of four indenyl doublets: δ 6.78 (J = 2.75 Hz, 1 H); 6.55 (J = 2.75 Hz, 1 H); 4.79 (J = 1.83 Hz, 1 H); 4.61 (J = 1.83 Hz, 1 H).
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    • note
    • The diastereoselective cyclization of an enyne by the rac-(EBTHI) moiety serves as an accurate model for the enantioselective cyclization of an enyne by the (S,S)-(EBTHI) moiety.


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