Communications
Measuring range 28 ꢁ q < 708, ꢀ13 ꢁ h ꢁ 13, ꢀ16 ꢁ k ꢁ 16,
ꢀ18 ꢁ l ꢁ 18. Measured reflex number: 14163, independent:
13426 (Rint = 0.0130), observed: 13229 (j F j /s(F) > 4.0). Correc-
tions: Lorentz and polarization correction. Intensity decline of
ca. 5% corrected with cubic spline; solution: program: SIR-92
(direct method), refinement: program: SHELXL-97.
CCDC 283243 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
Herein we have described a stereoselective approach to
the regioisomeric series of 6,7- and 7,8-benzomorphans
employing benzyl-substituted N-galactosyl didehydropiperi-
dinones. In both processes the galactosyl auxiliary exhibits
excellent stereo- and regiocontrol in the key steps. The
corresponding enantiomeric products are accessible by use of
the quasi-enantiomerc d-arabinosyl auxiliary.[18]
Received: November 17, 2005
[16] With long reaction times, cleavage of the 6-pivaloyl protecting
group (ca. 10%) from the cyclized product was observed.
[17] S. Scheibye, B. S. Pedersen, S.-O. Lawesson, Bull. Soc. Chim.
Belg. 1978, 87, 229 – 238.
[18] B. Kranke, D. Hebrault, M. Schultz-Kukula, H. Kunz, Synlett
2004, 671 – 674.
Published online: March 20, 2006
Keywords: aminoalkylation · asymmetric synthesis ·
.
benzomorphans · chiral auxiliaries · domino reactions
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[15] X-ray structure analysis of 15a (MeOH): triclinic, space group
P1, a = 10.951(2), b = 13.406(2), c = 15.086(3) , a = 105.61 (2),
b = 106.08(1), g = 104.65 (1)8. At
a cell volume of V=
1917.0(7) 3, two independent molecules and Mr = 685.83 results
in a density of d = 1.188 gcmꢀ3. Total number of electrons per
elemental cell FACHTREUNG(000) = 740. Diffractometer CAD4, CuKa graph-
ite monochromator. Scan type w/2q, scan width 0.9 + 0.15tan(q).
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Angew. Chem. Int. Ed. 2006, 45, 2623 –2626