Tandem Aza[4 + 2]/allylboration: A novel multicomponent reaction for the stereocontrolled synthesis of α-hydroxyalkyl piperidine derivatives

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3715-3718

  Tailor, Jyoti ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000418347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006626b     Document Type: Article

References (28)

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24. We suspect that dienes 1 are prone to thermal decomposition, thereby causing a reduction in the yield of desired product when used as limiting component. In the preparation of 1, minor amounts of the isomeric (Z)-vinylboronate was observed. Upon inspection of recovered material from incomplete aza[4 + 2]/allylboration reactions, this was shown not to affect the efficiency of the MCR, as no further isomerization of the diene was found.
25. -3. Data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-145481. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, U.K. (fax: (+44) 1223-336-033; E-mail: deposit@ccdc.cam.ac.uk).
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28. 13C NMR spectra by comparison with products from the cycloaddition of the non-methylated analogue of 6, which provided a 80% de. No related NMR signals of the minor isomer from the latter could be found in the crude spectra of 7.