Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 21, Pages 8833-8839Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2015483
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Funding
- Chinese National Science Foundation [81072528]
- Shanghai Commission of Science and Technology [10410702600, 10JC1417100, 10dz1910104]
- National Science & Technology Major Project on Key New Drug Creation and Manufacturing Program [2012ZX09101, 2009ZX09301-001, 2009ZX09103-062]
- Key Laboratory of Pesticide & Chemical Biology, Central China Normal University [201005A02]
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The cyclization reactions of arylamines with 2-deoxy-D-ribose or glycals were reinvestigated in the current report. In the montmorillonite KSF- or InCl3-initiated reactions of 2-deoxy-D-ribose with arylamines, a pair of diastereomeric tetrahydro-2H-pyran-fused tetrahydroquinolines was obtained in a nearly 1:1 ratio where the structure of one diastereomer was incorrectly assigned in the literature. Meanwhile, the diastereoselectivity in InBr3-catalyzed cyclization of glycals with arylamines was also incorrectly reported previously. It was found that high diastereomeric selectivity was achieved only when a CS substituted glycal was used; otherwise, a pair of diastereomers was obtained in moderate yield with 1:1 diastereomeric ratio. Furthermore, tetrahydrofuran-fused tetrahydroquinolines 5b and 5b' were also prepared successfully by using TBDPS-protected ribose as the glycal precursor and montmorillonite KSF as the activator.
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