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Volumn 134, Issue 9, 2012, Pages 4064-4067

Erratum: Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade (Journal of the American Chemical Society (2012) 134 (4064-4067) DOI: 10.1021/ja2119833);Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CHEMICAL ACTIVATION; RHODIUM COMPOUNDS;

EID: 84857887706     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja507742p     Document Type: Erratum
Times cited : (113)

References (69)
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    • A large and increasing number of reports on the synthesis of heterocycles involving C-H activation have been published in recent years. For examples, see the following publications and references therein: (a) Jayakumar, J.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 197.
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    • See the Supporting Information for the preparation of imines 1 and alkyne 4c. For some imines, E and Z isomers were observed by NMR spectroscopy. However, this did not affect the rate of C-H activation because isomerization is much more rapid than the activation reaction. For example, see
    • See the Supporting Information for the preparation of imines 1 and alkyne 4c. For some imines, E and Z isomers were observed by NMR spectroscopy. However, this did not affect the rate of C-H activation because isomerization is much more rapid than the activation reaction. For example, see: Jennings, W. B.; Boyd, D. R. J. Am. Chem. Soc. 1972, 94, 7187.
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    • note
    • 1H NMR spectroscopy for 6e, 6h, and 6n to exclude high dr's resulting from selective isolation of one diastereoisomer; they were found to be >95%. (b) When alkyne 2c was coupled with an α,β-unsaturated imine lacking γ-substitution, high regioselectivity was observed. See entry 2 in Table 2 of ref 3b. (c) The reduced yield was not due to selective isolation of 6k, as evidenced by crude NMR spectra.
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    • See the Supporting Information for ORTEP representations, details of the crystallographic analyses, and CIF files.
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    • Energetically, 7e is closer to 5e than to 4e, and it is therefore reasonable to assume structural similarity to 5e on the basis of the Hammond postulate.
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