The first metal-catalyzed intramolecular [5+2] cycloadditions of vinylcyclopropanes and alkenes: Scope, stereochemistry, and asymmetric catalysis

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 7203-7220

  Wender, Paul A ^a   Husfeld, Craig O ^a   Langkopf, Elke ^a   Love, Jennifer A ^a   Pleuss, Norbert ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPROPANE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032543523     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00355-X     Document Type: Article

References (80)

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67. [24] Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843. Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962. Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824.
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69. [25] For a review on metal-mediated cleavage of cyclopropanes, see Khusnutidinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 1 and references therein.
70. [26] Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720.
71. [27] For a preliminary communication on the transition metal-catalyzed [5+2] cycloadditions of alkenes, see: Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc., in press.
72. [28] For representative examples, see: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38, 3224. Gigg, R. J. Chem. Soc., Perkin Trans I 1980, 738.
73. [28] For representative examples, see: Corey, E. J.; Suggs, J. W. J. Org. Chem. 1973, 38, 3224. Gigg, R. J. Chem. Soc., Perkin Trans I 1980, 738.
74. [29] Wender, P. A.; Sperandio, D., Stanford University, unpublished results.
75. [30] The stereochemistry of 35 has been tentatively assigned by chemical correlation. Cis-fused cycloadduct 19 was converted in three steps to ketone 19a and its regioisomer 19a'. Hydrogenation of 19a and a' occurred with partial double bond isomerization and subsequent reduction to provide 19b and c, which are the cis and trans ring junction isomers. Cycloadduct 35 was converted to 35a. Hydrogenation of 35a provided a single isomer which co-eluted (by GC analysis) with 19c. (fomula presented)
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