Abstract
The enantioselective conjugate addition reaction of 3-substituted
oxindoles with 1,1-bis(benzenesulfonyl)ethylene by binaphthyl-modified
bifunctional organocatalysts was investigated. The corresponding
Michael adducts, containing a quaternary center at C3 position of
the oxindoles, were generally obtained in high yields with excellent
enantioselectivities (up to 99% ee).
Key words
oxindole - vinyl sulfone - conjugate addition - bifunctional organocatalysis - asymmetric
catalysis
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Typical Procedure
for the Conjugate Addition Reaction of 3-Phenyl Oxindole 1f with
Vinyl Sulfone 2
To a solution of 3-phenyl oxindole 1f (0.3 mmol, 92 mg) and catalyst VIII (0.03 mmol, 21.4 mg) in CH2Cl2 (1.2
mL) was added 1,1-bis(benzenesulfonyl)ethylene (2,
0.45 mmol, 138.7 mg). Reaction mixture was stirred for 6 h at r.t., concentrated,
and purified by flash column chromatography (EtOAc-hexane = 1:5)
to afford the Michael adduct (3f, 168 mg,
90%).
(
R
)-
tert
-Butyl 3-[2,2-bis(phenylsulfonyl)ethyl]-2-oxo-3-phenylindoline-1-carboxylate
(3f)
[α]D
²7 26.0
(c 0.4, CHCl3). ¹H
NMR (200 MHz, CDCl3): δ = 8.07-7.97
(m, 3 H), 7.77-7.67 (m, 3 H), 7.64-7.46 (m, 6
H), 7.38-7.16 (m, 7 H), 4.45-4.41 (m, 1 H), 3.40-3.29
(m, 2 H), 1.59 (s, 9 H). ¹³C NMR (50
MHz, CDCl3): δ = 175.2, 149.2, 141.2,
140.8, 138.0, 134.7, 134.4, 131.0, 129.3, 128.9, 128.8, 128.0, 126.7,
125.7, 124.6, 116.3, 84.3, 80.6, 55.2, 32.1, 28.0. HPLC [n-hexane-i-PrOH
(90:10), 254 nm, 0.5 mL/min] Chiralcel OD-H column, t
R = 18.8
min (major), t
R = 23.9
(minor), 95% ee.