Full Paper
[α]D20 = +66.9 (c = 1.0, CH2Cl2). IR (ATR): ν = 3330, 2930 cm–1 1H
.
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˜
NMR (300 MHz, CDCl3): δ = 1.69–1.79 (m, 1 H, CHaHbCHaHbOH),
1.79–2.10 (m, 4 H, 2 1-H, 2 2-H), 2.17–2.26 (m, 1 H, CHaHbCHaHbOH),
2.27–2.36 (m, 1 H, 3a-H), 2.55–2.64 (m, 1 H, 10a-H), 2.89–2.95 (m, 1
H, CHaHbCHaHbOH), 3.18–3.21 (m, 1 H, 10-H), 3.25–3.32 (m, 2 H, 3b-
H, CHaHbCHaHbOH), 3.37 (d, J = 14.3 Hz, 1 H, 5a-H), 3.84 (s, 3 H,
OCH3), 3.85 (s, 3 H, OCH3), 4.11 (d, J = 14.3 Hz, 1 H, 5b-H), 6.53 (s,
1 H, 6-H), 6.58 (s, 1 H, 9-H) ppm. 13C NMR (75.5 MHz, CDCl3): δ =
21.3 (C-2), 25.5 (C-1), 33.0 (CH2CH2OH), 39.7 (C-10), 54.6 (C-3), 55.5
(C-5), 55.8, 55.9 (2 OCH3), 56.9 (CH2CH2OH), 62.6 (C-10a), 108.9 (C-
6), 111.4 (C-9), 126.7 (C-5a), 128.7 (C-9a), 147.6, 147.9 (C-7, C-8) ppm.
MS (ESI): m/z (%) = 279 (14), 278 (100) [M + H]+. HRMS (ESI): calcd.
for C16H24NO3 [M + H]+ 278.1756; found 278.1760.
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Supporting Information (see footnote on the first page of this
article): Synthesis and characterization of precursors 1a–1f, 5a, and
5b; details of additional reactions carried out with 1e and with
electron-deficient heteroaryl halides; copies of 1H and 13C NMR
spectra of compounds described; X-ray crystallographic data for 6
and 7; and selected chiral stationary phase HPLC traces (see foot-
note on the first page of this article).
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Acknowledgments
Ministerio de Economía y Competitividad (MEC) (CTQ2013-
41229-P), Gobierno Vasco (IT-623-13), and Universidad del País
Vasco/Euskal Herriko Unibertsitatea UPV/EHU (UFI11/22,
PPM12/03) are gratefully acknowledged for their financial sup-
port. The authors also thank Gobierno Vasco for grants (to
A. R. A., E. C., and I. B.). Technical and human support provided
by Servicios Generales de Investigación SGIker (UPV/EHU, MIN-
ECO, GV/EJ, ERDF, and ESF) is also acknowledged.
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Keywords: Asymmetric synthesis · C–C coupling ·
Palladium · Nitrogen heterocycles
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