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S. Jiang et al. / Tetrahedron: Asymmetry 11 (2000) 3873–3877
Compounds 1–3 have been screened as herbicides. Unfortunately, these compounds did not
show any significant activity in the tests. Our current efforts are directed towards preparations
of other difluorinated carbasugars and also the further functionalisation of 3 into other useful
synthetic targets.
Acknowledgements
We thank Dr. Richard H. Wightman (Heriot-Watt University) and Dr. Xiangzhu Wang
(Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences) for helpful discussions,
and Dr. Franz Dorn (Novartis Crop Protection AG) for carrying out biological testing. We also
thank Jonathan Robinson for performing some initial experiments and the EPSRC for access to
the high resolution mass spectrometry service at the University of Wales, Swansea.
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1
9. All new compounds reported were fully characterised (IR, H and 13C NMR, HRMS and/or elemental analyses).
Selected data: Compound 3: wmax(KBr)/cm−1 3457, 3305, 2994, 2983, 2915, 2871, 1756 (CꢁO), 1382, 1224, 1091,
1068, 1024; lH (400 MHz, CDCl3) 1.39 (3H, s, Me), 1.52 (3H, s, Me), 2.18 (3H, s, COMe), 2.42−2.55 (1H, m,
CHCH2OH), 2.55 (3H, s, NMe), 3.00 (2H, br s, NH, OH), 3.27−3.31 (1H, m, CHNMe), 3.94 (1H, dd, J 11.9 and
3.9 Hz, CHHOH), 4.12 (1H, dd, J 11.9 and 6.3 Hz, CHHOH), 4.28 (1H, dd, J 6.9 and 5.5 Hz, CHORCHOAc),
4.37 (1H, apparent t, J 5.1 Hz, CHORCHN), 5.29 (1H, ddd, JFH 21.3 and 4.1 Hz, JHH 6.9 Hz, CHOAc); lC
(100.6 MHz, CDCl3) 20.67 (COMe), 26.08 (Me), 27.79 (Me), 35.15 (NMe), 41.81 (t, JFC 19.83 Hz, CHCH2OH),
59.00 (dd, JFC 4.32 and 4.19 Hz, CH2OH), 59.67 (d, CHN), 71.55 (dd, JFC 22.94 and 20.37 Hz, CHOAc), 74.35
(CHORCHN), 75.86 (d, JFC 4.88 Hz, CHORCHOAc), 110.25 (CMe2), 121.02 (dd, JFC 253.1 and 248.6 Hz, CF2),
169.57 (CꢁO); lF (376.5 MHz, CDCl3) −117.82 (ddd, JFF 256.9 Hz, JFH 26.1 and 21.8 Hz), −106.85 (dt, JFF 256.9
Hz, JFH 2.8 Hz) [m/z HRMS (CI, NH3). Found: MH+ 310.1466, C13H22F2NO5 requires 310.1466] (Found: C,