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9
Typical Procedure
for the Asymmetric Nitro-Mannich Reaction for the Synthesis of Compound
4a
To a mixture of α-amido sulfone 3a (0.1 mmol), chiral catalyst (S,S)-1d (0.005 mmol, 5 mol%), and K2CO3 (0.4 mmol)
in toluene (1.0 mL) at 0 ˚C was added nitroalkane 2a (0.2 mmol) in one portion. The resulting
mixture was stirred at 0 ˚C for 2 h. Then, a sat.
aq NH4Cl solution was added, and the organic layer was
extracted with EtOAc. The extracts were dried over MgSO4,
filtered, and concentrated in vacuo. Compound 4a was
obtained as a white solid in 76% yield after flash column
chromatography (PE-EtOAc = 50:1), and
the ee was determined to be 86% by HPLC on Chiralpak AD-H
column (15% 2-PrOH-n-hexane,
1 mL/min), λ = 220 nm, t
R (major) = 15.9
min, t
R minor) = 17.8 min;
mp 189-190 ˚C. ¹H
NMR (500 MHz, CDCl3): δ = 7.33-7.41
(m, 3 H), 7.26-7.31 (m, 4 H), 7.12-7.25 (m, 3 H),
5.19-5.30 (m, 2 H), 4.99-5.10 (br s, 1 H), 3.25-3.35
(m, 1 H), 3.13-3.20 (dd, J = 3.5,
14.8 Hz, 1 H), 1.46 (s, 9 H) ppm. ¹³C
NMR (125 MHz, CDCl3): δ = 155.0,
136.4, 135.5, 129.2, 129.0, 128.9, 128.8, 127.5, 127.0, 92.7, 80.8,
57.3, 36.2, 28.2 ppm. ESI-HRMS: m/z calcd
for C20H24N2O4 + Na: 379.1634;
found: 379.1636.