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Isolation: Ref. 12a.
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(a) Isolation: Ref. 12a.
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37
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(b) Recent synthesis and references to earlier syntheses: Ref. 4e.
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For improved one-pot oxidative conditions (Jones reagent) that transform this heterocycle into N-Boc glycinate without epimerization, see: (a)
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2, 0 (C, 1 h). The high reactivity of tert-butyl ester groups at C3 and C5 may be attributed to the strong conjugation with the adjacent carbon-carbon double bond of the enaminic system. This speculation is supported by the unreactivity under the above acidic conditions of tert-butyl ester groups installed at C3 and C5 of pyridyl and 1-oxido-pyridyl rings. For a discussion about this issue, see: (a)
-
2, 0 (C, 1 h). The high reactivity of tert-butyl ester groups at C3 and C5 may be attributed to the strong conjugation with the adjacent carbon-carbon double bond of the enaminic system. This speculation is supported by the unreactivity under the above acidic conditions of tert-butyl ester groups installed at C3 and C5 of pyridyl and 1-oxido-pyridyl rings. For a discussion about this issue, see: (a) Goerlitzer K., Baltrusch H. J. Pharmazie. 10:2000;747-750.
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85030904577
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note
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Complete crystallographic data (excluding structural factors) for the structure of the (R)-Mosher's amide of (4R)-27a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications number CCDC 222942. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
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