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DOI: 10.1055/s-0030-1260770
Highly Enantioselective Conjugate Addition of 3-Substituted Oxindoles to Vinyl Sulfone Catalyzed by Binaphthyl-Modified Tertiary Amines
Publication History
Publication Date:
01 June 2011 (online)
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
- For selected reviews, see:
- 1a
Marti C.Carreira EM. Eur. J. Org. Chem. 2003, 2209 - 1b
Dounay AB.Overman LE. Chem. Rev. 2003, 103: 2945 - 1c
Galliford CV.Scheidt KA. Angew. Chem. Int. Ed. 2007, 46: 8748 - 1d
Trost BM.Brennan MK. Synthesis 2009, 3003 - For reviews, see:
- 2a
Dounay AB.Overman LE. Chem. Rev. 2003, 103: 2945 - 2b
Galliford CV.Scheidt KA. Angew. Chem. Int. Ed. 2007, 46: 8748 - 2c
Lin H.Danishefsky SJ. Angew. Chem. Int. Ed. 2003, 42: 36 - 2d
Rahman AU.Basha A. Indole Alkaloids Harwood Academic Publishers; Amsterdam: 1997. - 2e
Zhou F.Liu Y.-L.Zhou J. Adv. Synth. Catal. 2010, 352: 1381 - 3a
Mouri S.Chen Z.Mitsunuma H.Furutachi M.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2010, 132: 1255 - 3b
Kato Y.Furutachi M.Chen Z.Mitsunuma H.Matsunaga S.Shibasaki M. J. Am. Chem. Soc. 2009, 131: 9168 - 3c
Tomita D.Yamatsugu K.Kanai M.Shibasaki M. J. Am. Chem. Soc. 2009, 131: 6946 - 3d
Linton EC.Kozlowski MC. J. Am. Chem. Soc. 2008, 130: 16162 - 3e
Kundig EP.Seidel TM.Jia Y.-X.Bernardinelli G. Angew. Chem. Int. Ed. 2007, 46: 8484 - 3f
Shintani R.Inoue M.Hayashi T. Angew. Chem. Int. Ed. 2006, 45: 3353 - 3g
Dounay AB.Hatanaka K.Kodanko JJ.Oestreich M.Overman LE.Pfeifer LA.Weiss MM. J. Am. Chem. Soc. 2003, 125: 6261 - 3h
Trost BM.Frederiksen MU. Angew. Chem. Int. Ed. 2005, 44: 308 - 3i
Trost BM.Zhang Y. Chem. Eur. J. 2010, 16: 296 - 3j
Trost BM.Zhang Y. J. Am. Chem. Soc. 2007, 129: 14548 - 3k
Hamashima Y.Suzuki T.Takano H.Shimura Y.Sodeoka M. J. Am. Chem. Soc. 2005, 127: 10164 - 3l
Corkey BK.Toste FD. J. Am. Chem. Soc. 2007, 129: 2764 - 3m
Jia Y.-X.Hillgren JM.Watson EL.Marsden SP.Kundig EP. Chem. Commun. 2008, 4040 - 3n
Lee S.Hartwig JF. J. Org. Chem. 2001, 66: 3402 - 3o
Trost BM.Czabaninuk LC. J. Am. Chem. Soc. 2010, 132: 15534 - 4a
Bui T.Syed S.Barbas CF. J. Am. Chem. Soc. 2009, 131: 8758 - 4b
Galzerano P.Bencivenni G.Pesciaioli F.Mazzanti A.Giannichi B.Sambri L.Bartoli G.Melchiorre P. Chem. Eur. J. 2009, 15: 7846 - 4c
Bravo N.Mon I.Companyo X.Alba A.-N.Moyano A.Rios R. Tetrahedron Lett. 2009, 50: 6624 - 4d
Li X.Zhang B.Xi Z.-G.Luo S.Cheng J.-P. Adv. Synth. Catal. 2010, 352: 416 - 4e
Li X.Xi Z.-G.Luo S.Cheng J.-P. Org. Biomol. Chem. 2010, 8: 77 - 4f
Pesciaioli F.Tian X.Bencivenni G.Bartoli G.Melchiorre P. Synlett 2010, 1704 - For reviews, see:
- 5a
Simpkins NS. Tetrahedron 1990, 46: 6951 - 5b
Najera C.Yus M. Tetrahedron 1999, 55: 10547 - 5c
Nielsen M.Jacobsen CB.Holub N.Paixao MW.Jørgensen KA. Angew. Chem. Int. Ed. 2010, 49: 2668 - 5d
Zhu Q.Lu Y. Aust. J. Chem. 2009, 62: 95 - 5e
Alba A.-NR.Companya X.Rios R. Chem. Soc. Rev. 2010, 39: 2018 - 6a
Zhu Q.Lu Y. Org. Lett. 2008, 10: 4803 - 6b
Zhu Q.Cheng L.Lu Y. Chem. Commun. 2008, 6315 - 6c
Zhu Q.Lu Y. Org. Lett. 2009, 11: 1721 - 6d
Zhu Q.Lu Y. Chem. Commun. 2010, 46: 2235 - 6e
Li H.Song J.Liu X.Deng L. J. Am. Chem. Soc. 2005, 127: 8948 - 6f
Li H.Song J.Deng L. Tetrahedron 2009, 65: 3139 - 6g
Moss S.Alexakis A. Org. Lett. 2005, 7: 4361 - 6h
Quintard A.Bournaud C.Alexakis A. Chem. Eur. J. 2008, 14: 7504 - 6i
Quintard A.Alexakis A. Chem. Eur. J. 2009, 15: 11109 - 6j
Sulzer-Moss S.Alexakis A.Mareda J.Bollot G.Bernardinelli G.Filinchuk Y. Chem. Eur. J. 2009, 15: 3204 - 6k
Quintard A.Belot S.Sebastien M.Marchal E.Alexakis A. Eur. J. Org. Chem. 2010, 927 - 6l
Quintard A.Alexakis A. Chem. Commun. 2010, 46: 4085 - 6m
Landa A.Maestro M.Masdeu C.Puente A.Vera S.Oiarbide M.Palomo C. Chem. Eur. J. 2009, 15: 1562 - 6n
Liu T.-Y.Long J.Li B.-J.Jiang L.Li R.Wu Y.Ding L.-S.Chen Y.-C. Org. Biomol. Chem. 2006, 4: 2097 - 6o
Alba A.-NR.Companyo X.Valero G.Moyano A.Rios R. Chem. Eur. J. 2010, 16: 5354 - 6p
Alemn J.Reyes E.Richter B.Overgaard J.Jørgensen KA. Chem. Commun. 2007, 3921 - 6q
Moteki SA.Xu S.Arimitsu S.Maruoka K. J. Am. Chem. Soc. 2010, 132: 17074 - 7
Zhu Q.Lu Y. Angew. Chem. Int. Ed. 2010, 49: 7753 - 8a
Park EJ.Kim MH.Kim DY. J. Org. Chem. 2004, 69: 6897 - 8b
Kang YK.Kim DY. Bull. Korean Chem. Soc. 2008, 29: 2093 - 8c
Lee JH.Kim DY. Adv. Synth. Catal. 2009, 351: 1779 - 8d
Kang YK.Kim DY. J. Org. Chem. 2009, 74: 5734 - 8e
Lee JH.Kim DY. Synthesis 2010, 1860 - 8f
Kang YK.Kim DY. Curr. Org. Chem. 2010, 14: 917 - 9a
Moon HW.Cho MJ.Kim DY. Tetrahedron Lett. 2009, 50: 4896 - 9b
Moon HW.Kim DY. Tetrahedron Lett. 2010, 51: 2906 - 9c
Moon HW.Kim DY. Bull. Korean Chem. Soc. 2011, 32: 291 - 9d
Kang YK.Kim SM.Kim DY. J. Am. Chem. Soc. 2010, 132: 11847 - 10a
Mang JY.Kim DY. Bull. Korean Chem. Soc. 2008, 29: 2091 - 10b
Kim SM.Lee JH.Kim DY. Synlett 2008, 2659 - 10c
Jung SH.Kim DY. Tetrahedron Lett. 2008, 49: 5527 - 10d
Kwon BK.Kim SM.Kim DY.
J. Fluorine Chem. 2009, 130: 759 - 10e
Oh Y.Kim SM.Kim DY. Tetrahedron Lett. 2009, 50: 4674 - 10f
Kwon BK.Kim DY. Bull. Korean Chem. Soc. 2009, 30: 1441 - 10g
Yoon SJ.Kang YK.Kim DY. Synlett 2011, 420 - For selected examples of asymmetric catalysis with chiral squaramide-derived catalysts, see:
- 11a
Malerich JP.Hagihara K.Rawal VH. J. Am. Chem. Soc. 2008, 130: 14416 - 11b
Zhu Y.Malerich JP.Rawal VH. Angew. Chem. Int. Ed. 2010, 49: 153 - 11c
Konishi H.Lam TY.Malerich JP.Rawal VH. Org. Lett. 2010, 12: 2028 - 11d
Qian Y.Ma G.Lv A.Zhu H.-L.Zhao J.Rawal VH. Chem. Commun. 2010, 46: 3004 - 11e
Dai L.Wang S.-X.Chen F.-E. Adv. Synth. Catal. 2010, 352: 2137 - 11f
Jiang H.Paixão MW.Monge D.Jørgensen KA. J. Am. Chem. Soc. 2010, 132: 2775
References and Notes
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.