SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 4, 2009, Pages 664-666

Enantioselective alkylation of α-fluoro-β-keto esters by asymmetric phase-transfer catalysis

(2) Ding, Changhua a Maruoka, Keiji a

a KYOTO UNIVERSITY (Japan)

Author keywords

Alkyl halides; Alkylations; Asymmetric catalysis; Esters; Phase transfer catalysis

Indexed keywords

EID: 62249108716 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087813 Document Type: Article

Times cited : (29)

References (41)

1
- 0003661703
- For general reviews, see: a
- For general reviews, see: (a) Mann, J. Chem. Soc. Rev. 1987, 16, 381.
- (1987) Chem. Soc. Rev , vol.16 , pp. 381
- Mann, J.¹

2
- 0023237559
- (b) Welch, J. T. Tetrahedron 1987, 43, 3123.
- (1987) Tetrahedron , vol.43 , pp. 3123
- Welch, J.T.¹

3
- 35248848834
- Selective Fluorination
- American Chemical Society: Washington DC
- (c) Welch, J. T. Selective Fluorination, ACS Symposium Series 456; American Chemical Society: Washington DC, 1991.
- (1991) ACS Symposium Series , vol.456
- Welch, J.T.¹

4
- 1542534457
- (d) Wilkinson, J. A. Chem. Rev. 1992, 92, 505.
- (1992) Chem. Rev , vol.92 , pp. 505
- Wilkinson, J.A.¹

5
- 0003490830
- Elsevier: Amsterdam
- (e) Filler, R.; Kobayashi, Y.; Yagupolskii, Y. L. Organofluorine Compounds in Medicinal Chemistry and Biological Applications; Elsevier: Amsterdam, 1993.
- (1993) Organofluorine Compounds in Medicinal Chemistry and Biological Applications
- Filler, R.¹ Kobayashi, Y.² Yagupolskii, Y.L.³

6
- 0003536898
- Plenum Press: New York
- (f) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994.
- (1994) Organofluorine Chemistry: Principles and Commercial Applications
- Banks, R.E.¹ Smart, B.E.² Tatlow, J.C.³

7
- 0003132813
- Chemistry of Organic Fluorine Compounds II. A Critical Review
- American Chemical Society: Washington DC
- (g) Hudlicky, M.; Pavlath, A. E. Chemistry of Organic Fluorine Compounds II. A Critical Review, ACS Monograph 187; American Chemical Society: Washington DC, 1995.
- (1995) ACS Monograph , vol.187
- Hudlicky, M.¹ Pavlath, A.E.²

8
- 0003518240
- Ojima, I, McCarthy, J. R, Welch, J. T, Eds, American Chemical Society: Washington DC
- (h) Biomedical Frontiers of Fluorine Chemistry; Ojima, I.; McCarthy, J. R.; Welch, J. T., Eds.; American Chemical Society: Washington DC, 1996.
- (1996) Biomedical Frontiers of Fluorine Chemistry

9
- 0003508266
- Hiyama, T, Ed, Springer: New York
- (i) Organofluorine Compounds. Chemistry and Applications; Hiyama, T., Ed.; Springer: New York, 2000.
- (2000) Organofluorine Compounds. Chemistry and Applications

10
- 0000532882
- (a) Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661.
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 661
- Bravo, P.¹ Resnati, G.²

11
- 0027432004
- (b) Resnati, G. Tetrahedron 1993, 49, 9385.
- (1993) Tetrahedron , vol.49 , pp. 9385
- Resnati, G.¹

12
- 62249185435
- Hayashi T., Soloshonok V. A., Eds. Tetrahedron: Asymmetry 1994, 5, 955.
- (c) Hayashi T., Soloshonok V. A., Eds. Tetrahedron: Asymmetry 1994, 5, 955.

13
- 0032512020
- (d) Iseki, K. Tetrahedron 1998, 54, 13887.
- (1998) Tetrahedron , vol.54 , pp. 13887
- Iseki, K.¹

14
- 0003481072
- Wiley: Chichester
- (e) Soloshonok, V. A. Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Wiley: Chichester, 1999.
- (1999) Enantiocontrolled Synthesis of Fluoro-Organic Compounds
- Soloshonok, V.A.¹

15
- 0002780706
- Asymmetric Fluoroorganic Chemistry. Synthesis, Applications, and Future Directions
- Ramachandran, P. V, Ed, American Chemical Society: Washington DC
- (f) Asymmetric Fluoroorganic Chemistry. Synthesis, Applications, and Future Directions, ACS Symposium Series 746; Ramachandran, P. V., Ed.; American Chemical Society: Washington DC, 2000.
- (2000) ACS Symposium Series , vol.746

16
- 11144341001
- (a) Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119.
- (2004) Chem. Rev , vol.104 , pp. 6119
- Ma, J.-A.¹ Cahard, D.²

17
- 31044445377
- (b) Pihko, P. M. Angew. Chem. Int. Ed. 2006, 45, 544.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 544
- Pihko, P.M.¹

18
- 33746318363
- (c) Prakash, G. K.; Beier, S. P. Angew. Chem. Int. Ed. 2006, 45, 2172.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 2172
- Prakash, G.K.¹ Beier, S.P.²

19
- 33744802202
- (d) Bobbio, C.; Gouverneur, V. Org. Biomol. Chem. 2006, 4, 2065.
- (2006) Org. Biomol. Chem , vol.4 , pp. 2065
- Bobbio, C.¹ Gouverneur, V.²

20
- 34247114685
- (e) Shibata, N.; Ishimaru, T.; Nakamura, S.; Toru, T. J. Fluorine Chem. 2007, 128, 469.
- (2007) J. Fluorine Chem , vol.128 , pp. 469
- Shibata, N.¹ Ishimaru, T.² Nakamura, S.³ Toru, T.⁴

21
- 41249087594
- and references cited therein
- (f) Brunet, V. A.; O'Hagan, D. Angew. Chem. Int. Ed. 2008, 47, 1179; and references cited therein.
- (2008) Angew. Chem. Int. Ed , vol.47 , pp. 1179
- Brunet, V.A.¹ O'Hagan, D.²

22
- 0037065341
- See also: g
- See also: (g) Hamashima, Y.; Yagi, K.; Takano, H.; Tamás, L.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 14530.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 14530
- Hamashima, Y.¹ Yagi, K.² Takano, H.³ Tamás, L.⁴ Sodeoka, M.⁵

23
- 0037148980
- (h) Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
- (2002) Org. Lett , vol.4 , pp. 545
- Kim, D.Y.¹ Park, E.J.²

24
- 38349148300
- For recent reviews, see: a
- For recent reviews, see: (a) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656.
- (2007) Chem. Rev , vol.107 , pp. 5656
- Hashimoto, T.¹ Maruoka, K.²

25
- 34447272888
- (b) Ooi, T.; Maruoka, K. Angew. Chem. Int. Ed. 2007, 46, 4222.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 4222
- Ooi, T.¹ Maruoka, K.²

26
- 35048900464
- (c) Ooi, T.; Maruoka, K. Aldrichimica Acta 2007, 40, 77.
- (2007) Aldrichimica Acta , vol.40 , pp. 77
- Ooi, T.¹ Maruoka, K.²

27
- 34147215084
- (d) Maruoka, K.; Ooi, T.; Kano, T. Chem. Commun. 2007, 1487.
- (2007) Chem. Commun , pp. 1487
- Maruoka, K.¹ Ooi, T.² Kano, T.³

28
- 0034738068
- (a) Ooi, T.; Takeuchi, M.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2000, 122, 5228.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 5228
- Ooi, T.¹ Takeuchi, M.² Kameda, M.³ Maruoka, K.⁴

29
- 0034699788
- (b) Ooi, T.; Kameda, M.; Tannai, H.; Maruoka, K. Tetrahedron Lett. 2000, 41, 8339.
- (2000) Tetrahedron Lett , vol.41 , pp. 8339
- Ooi, T.¹ Kameda, M.² Tannai, H.³ Maruoka, K.⁴

30
- 0034847347
- (c) Ooi, T.; Takeuchi, M.; Maruoka, K. Synthesis 2001, 1716.
- (2001) Synthesis , pp. 1716
- Ooi, T.¹ Takeuchi, M.² Maruoka, K.³

31
- 0037473547
- (d) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 5139.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 5139
- Ooi, T.¹ Kameda, M.² Maruoka, K.³

32
- 0842283440
- (e) Ooi, T.; Uematsu, Y.; Maruoka, K. Tetrahedron Lett. 2004, 45, 1675.
- (2004) Tetrahedron Lett , vol.45 , pp. 1675
- Ooi, T.¹ Uematsu, Y.² Maruoka, K.³

33
- 3242721636
- (f) Ooi, T.; Kameda, M.; Fujii, J.-i.; Maruoka, K. Org. Lett. 2004, 6, 2397.
- (2004) Org. Lett , vol.6 , pp. 2397
- Ooi, T.¹ Kameda, M.² Fujii, J.-I.³ Maruoka, K.⁴

34
- 3242877414
- (g) Jew, S.-s.; Lee, Y.-J.; Lee, J.; Kang, M. J.; Jeong, B.-S.; Lee, J.-H.; Yoo, M.-S.; Kim, M.-J.; Choi, S.-h.; Ku, J.-M.; Park, H.-g. Angew. Chem. Int. Ed. 2004, 43, 2382.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2382
- Jew, S.-S.¹ Lee, Y.-J.² Lee, J.³ Kang, M.J.⁴ Jeong, B.-S.⁵ Lee, J.-H.⁶ Yoo, M.-S.⁷ Kim, M.-J.⁸ Choi, S.-H.⁹ Ku, J.-M.¹⁰ Park, H.-G.¹¹

35
- 13444283787
- Maeda, K.; Miller, R. A.; Szumigala, R. H. Jr.; Shafiee, A.; Karady, S.; Armstrong, J. D. III Tetrahedron Lett. 2005, 46, 1545.
- (h) Maeda, K.; Miller, R. A.; Szumigala, R. H. Jr.; Shafiee, A.; Karady, S.; Armstrong, J. D. III Tetrahedron Lett. 2005, 46, 1545.

36
- 23044473705
- (i) Lee, Y.-J.; Lee, J.; Kim, M.-J.; Jeong, B.-S.; Lee, J.-H.; Kim, T.-S.; Lee, J.; Ku, J.-M.; Jew, S.-s.; Park, H.-g. Org. Lett. 2005, 7, 3207.
- (2005) Org. Lett , vol.7 , pp. 3207
- Lee, Y.-J.¹ Lee, J.² Kim, M.-J.³ Jeong, B.-S.⁴ Lee, J.-H.⁵ Kim, T.-S.⁶ Lee, J.⁷ Ku, J.-M.⁸ Jew, S.-S.⁹ Park, H.-G.¹⁰

37
- 33750014969
- (j) Kim, T.-S.; Lee, Y.-J.; Jeong, B.-S.; Park, H.-g.; Jew, S.-s. J. Org. Chem. 2006, 71, 8276.
- (2006) J. Org. Chem , vol.71 , pp. 8276
- Kim, T.-S.¹ Lee, Y.-J.² Jeong, B.-S.³ Park, H.-G.⁴ Jew, S.-S.⁵

38
- 0041363231
- (a) Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Angew. Chem. Int. Ed. 2003, 42, 3796.
- (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3796
- Ooi, T.¹ Miki, T.² Taniguchi, M.³ Shiraishi, M.⁴ Takeuchi, M.⁵ Maruoka, K.⁶

39
- 13444267639
- (b) Ooi, T.; Miki, T.; Maruoka, K. Org. Lett. 2005, 7, 191.
- (2005) Org. Lett , vol.7 , pp. 191
- Ooi, T.¹ Miki, T.² Maruoka, K.³

40
- 33748283341
- (c) Ooi, T.; Miki, T.; Fukumoto, K.; Maruoka, K. Adv. Synth. Catal. 2006, 348, 1539.
- (2006) Adv. Synth. Catal , vol.348 , pp. 1539
- Ooi, T.¹ Miki, T.² Fukumoto, K.³ Maruoka, K.⁴

41
- 62249113725
- Typical Procedure for the Catalytic Asymmetric Alkylation of tert-Butyl 2-Fluoro-3-oxo-3-phenylpropanoate (2b) under Phase-Transfer Conditions To a solution of phase-transfer catalyst (S,S)-1 (0.001 mmol, 0.9 mg) and 2b (0.10 mmol, 23.6 mg) in mesitylene (2 mL) was added benzyl bromide (0.12 mmol, 14.0 μL, and the mixture was cooled to 0°C. After adding 10% aq CsOH (0.3 mL, ca. 0.2 mmol) to this mixture, the reaction mixture was vigorously stirred until the completion of the reaction. The mixture was then poured into sat. aq NH 4Cl and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on SiO2 to give tert-butyl 2-benzyl-2-fluoro-3-oxo-3-phenylpropanoate (3b) as a colorless oil [82, 26.8 mg, 85% ee, Enantiomeric purity was determined by HPLC analysis [Daicel Chiralpak OD, hexane-2-PrOH 3
- 2), 1.29 (9 H, s, t-Bu).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.