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SO2Ph
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R1
C2H5
R1
C2H5
N
H
N
H
O
O
OTBDMS
OTBDMS
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8: R=
9: R=
H
H
10: R=
11: R=
H
H
ii
R1
C2H5
N
H
OH
12: R=
13: R=
H (-)-β-Conhydrine
H (-)-α-Conhydrine
Scheme 2. Reagents and conditions: (i) Na/Hg/MeOH; (ii) LiAlH4, THF/t-butylm-
ethyl ether.
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HPLC (chiracel column) and the optical rotation values (vide infra)
with those of well-known authentic compounds. To this aim and in
order to demonstrate the synthetic utility of our approach, herein
described, the elaboration of the HDA-adducts 8 and 9 to the cor-
responding conhydrines 12 and 13 in optically pure form was per-
formed through a simple protocol. In detail, treatment of the
intermediates 8 and 9 with sodium amalgam in methanol gave rise
to the corresponding pyridin-2-ones 10 and 11 in 77% yields.
Exhaustive reduction by LiAlH4 furnished the target compounds
12 in 68% and 13 in 74% yields, respectively (Scheme 2).30
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Supplementary data
optically active form, in 73% yield from commercially available
a-hydroxy acid
according: (a) Ahmed, F.; Al-Mutairi, E. H.; Avery, K. L.; Cullis, P. M.; Primrose,
W. U.; Roberts, G. C. K.; Willis, C. L. Chem. Commun. 1999, 2049–2050; See also:
(b) Moore, G. C.; Murphy, P. J.; Williams, H. L.; McGownb, A. T.; Smith, N. K.
Tetrahedron 2007, 63, 11771–11780.
Supplementary data associated with this article can be found, in
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References and notes
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