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Volumn 64, Issue 11, 1999, Pages 4206-4210

Stereospecific exo-selective Diels-Alder reactions with carbohydrate- functionalized α-exo-methylene-2-oxacyclopentylidene chromium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLENE 2 OXACYCLOPENTYLIDENE; CARBOHYDRATE DERIVATIVE; CHROMIUM DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; FUNCTIONAL GROUP; GALACTOPYRANOSE; UNCLASSIFIED DRUG;

EID: 0033612202     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982427i     Document Type: Article
Times cited : (26)

References (58)
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    • Recently, we have reported on the photochemical activation of α-exo-alkylidene 2-oxacycloalkylidene complexes for benzannulation leading to 2,3-dihydro-5-benzofuranol and chroman-6-ol skeletons: (a) Weyershausen, B.; Dötz, K. H. Eur. J. Org. Chem. 1998, 1739, 9. (b) Weyershausen, B.; Dötz, K. H. Synlett 1999, 231.
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    • For rare examples of exo-selective Diels-Alder reactions with Fischer-type ylidene complexes, see: (a) Anderson, B. A.; Wulff, W. D.; Powers, T. S.; Tribitt, S.; Rheingold, A. L. J. Am. Chem. Soc. 1992, 114, 10784. (b) Powers, T. S.; Jiang, W.; Su. J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438. (c) Barluenga, J.; Aznar, F.; Barluenga, S.; García-Granda, S.; Alvarez-Rúa, C. Synlett 1997, 1040.
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    • For rare examples of exo-selective Diels-Alder reactions with Fischer-type ylidene complexes, see: (a) Anderson, B. A.; Wulff, W. D.; Powers, T. S.; Tribitt, S.; Rheingold, A. L. J. Am. Chem. Soc. 1992, 114, 10784. (b) Powers, T. S.; Jiang, W.; Su. J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438. (c) Barluenga, J.; Aznar, F.; Barluenga, S.; García-Granda, S.; Alvarez-Rúa, C. Synlett 1997, 1040.
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    • For rare examples of exo-selective Diels-Alder reactions with Fischer-type ylidene complexes, see: (a) Anderson, B. A.; Wulff, W. D.; Powers, T. S.; Tribitt, S.; Rheingold, A. L. J. Am. Chem. Soc. 1992, 114, 10784. (b) Powers, T. S.; Jiang, W.; Su. J.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 6438. (c) Barluenga, J.; Aznar, F.; Barluenga, S.; García-Granda, S.; Alvarez-Rúa, C. Synlett 1997, 1040.
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    • 1H NMR spectra for 4R/S could be obtained because of the instability of these complexes
    • 1H NMR spectra for 4R/S could be obtained because of the instability of these complexes.
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    • note
    • The numbering of the atoms of complex 9 used in the text is not in accordance with that used in the ORTEP plot. Atoms C/H-4′ (text) correspond to C/H-1′ (ORTEP), atoms C/H-5′ (text) correspond to C/H-2′ (ORTEP), and C/H-6′ (text) correspond to C/H-3′ (ORTEP).
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