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Volumn 119, Issue 11, 1997, Pages 2597-2605

Asymmetric photocycloadditions with an optically active allenylsilane: Trimethylsilyl as a removable stereocontrolling group for the enantioselective synthesis of exo-methylenecyclobutanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE;

EID: 0030936921     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963436g     Document Type: Article
Times cited : (91)

References (68)
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    • (1993) Synlett , pp. 71
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    • This nomenclature parallels that which has been used in auxiliary-based enolate alkylation reactions; see: Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Stereodifferentiating Addition Reactions Part B; Wiley: New York, 1984; Vol. 3, Chapter 1.
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    • This is an example of chirality transfer that has been termed by Mislow as self-immolative; see: Mislow, K. Introduction to Stereochemistry; Benjamin: New York, 1965; p 131.
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    • note
    • 19F NMR resonances for the derived (S)-MTPA ester were poorly resolved to give an estimated 80-85% ee in the product.
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    • note
    • The absolute stereochemistry of the adducts is presumed to parallel that previously reported for the tert-butyl-substituted allenes, for which X-ray crystallographic analysis of an appropriate derivative was possible (ref 8). To date, we have been unable to obtain crystalline material of adducts 13-17 and their derivatives.
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    • note
    • Although the triisopropyl-substituted allenes typically gave products with higher levels of induction than the corresponding trimethylsilyl-substituted allenes, the desilylation of these photoadducts proceeded in diminished yields. We are currently investigating this novel class of allenes, and their synthetic chemistry which will be the subject of future work in our laboratories.
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    • (c) For recent investigations which provide verification to the rule of five, see: Maradyn, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5359.
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    • For mechanistic investigations of alkene-enone photocycloadditions, see: (a) Andrew, D.; Weedon, A. C. J. Am. Chem. Soc. 1995, 117, 5647. (b) Haddad, N.; Abramovich, Z. J. Org. Chem. 1995, 60, 6883. For computational studies, see: (c) Broeker, J. L.; Eksterowicz, J. E.; Belk, A. J.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 1847.
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    • For an example in which retroaddition competes with ring closure, see: (a) McCullough, J. J.; Ramachandran, B. R.; Snyder, F. F.; Taylor, G. N. J. Am. Chem. Soc. 1975, 97, 6767. (b) Hastings, D. J.; Weedon, A. C. J. Am. Chem. Soc. 1991, 113, 8525. (c) Maradyn, D. J.; Sydnes, L. K., Weedon, A. C. Tetrahedron Lett. 1993, 34, 2413. (d) Rudolph, A.; Weedon, A. C. Can. J. Chem. 1990, 68, 1590.
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    • For a discussion of the relative orientation between alkene and enone, and the resulting consequences in the stereochemistry of the photoadducts, see ref 19.
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    • note
    • It is important to note that formation of the first spirocyclic ring from 22a and 25c, for example, is an exothermic process and likely proceeds through an early transition state that should not resemble the cis-or transfused, 4-5 ring systems present in the ultimate products 24 and 27, respectively.
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    • Similar issues in the addition of allylmetal reagents to aldehydes have been discussed. For a leading reference, see: Keck, G. E.; Dougherty, S. M.; Savin, K. A. J. Am. Chem. Soc. 1995, 117, 6210.
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    • note
    • The calculation of the LUMO of 13 was performed using AM1 semiempirical methods supported by the Spartan molecular modeling package available from Wavefunction, Inc., Irvine, CA.


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