One-pot synthesis of highly functionalized morphans from C-glycosides

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DOIResolve DOI: http://doi.org/10.1016/j.carres.2009.08.028
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TypeArticle
Journal titleCarbohydrate Research
Volume344
Issue16
Pages21442150; # of pages: 7
SubjectSynthesis; Morphan; Tandem reaction; C-Glycoside
AbstractHighly functionalized morphan derivatives were synthesized from nitroalkene 2'-(oxoalkyl)-C-glycosides by a tandem reaction that created three (two C–N and one C–C) new bonds and four stereogenic centers in a one-pot procedure under very mild conditions without the use of expensive reagents. The transformation was achieved from a β-elimination/Michael addition cascade, followed by Michael addition of the amine and intramolecular enamination. In the presence of sodium cyanoborohydride the iminium intermediate was reduced in situ to afford the desired morphans.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Biological Sciences
Peer reviewedNo
NPARC number15329245
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Record identifierf0a0c5b9-ffee-4abc-83df-2f6969d02105
Record created2010-05-21
Record modified2016-05-09
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