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Volumn 118, Issue 8, 1996, Pages 1917-1930

π-Facial diastereoselection in the 1,2-addition of allylmetal reagents to 2-methoxycyclohexanone and tetrahydrofuranspiro-(2-cyclohexanone)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; SPIRO COMPOUND; TETRAHYDROFURAN DERIVATIVE;

EID: 0029873889     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9536835     Document Type: Article
Times cited : (90)

References (91)
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    • This reaction has been previously conducted in refluxing ether. Under these circumstances, the 12/13 composition is 6.6:1 [Negn. J. T., Paquette, L. A. J. Am. Chem. Soc: 1992, 114. 8835).
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    • Ph.D. Thesis, University of Wisconsin-Madison
    • Haight, A. R. Ph.D. Thesis, University of Wisconsin-Madison, 1990. We thank Prof. E. Vedejs for making the relevant pan of this thesis available to us.
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    • 2-tert-Butylcyclohexanone is reported to reside predominantly in the twist conformation: ref 34. p 733
    • 2-tert-Butylcyclohexanone is reported to reside predominantly in the twist conformation: ref 34. p 733.
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    • note
    • In actuality, the signal for H-6a is overlapped by those for H-3e and H-6e However, these protons cannot exert an effect on C-7 resulting from heteronuclear coupling
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    • note
    • We thank Mr. Anthony Lombardo for performing this experiment.


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