메뉴 건너뛰기




Volumn 121, Issue 39, 1999, Pages 9233-9234

Synthesis of chiral diaryliodonium salts, 1,1'-binaphthyl-2- yl(phenyl)iodonium tetrafluoroborates: Asymmetric α-phenylation of β-keto ester enolates [8]

Author keywords

[No Author keywords available]

Indexed keywords

BORINIC ACID DERIVATIVE; DIPHENYLIODONIUM SALT;

EID: 0032830171     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992236c     Document Type: Letter
Times cited : (141)

References (43)
  • 1
    • 0345664280 scopus 로고
    • Wiley: New York, Chapter 25
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1983) The Chemistry of Functional Groups , Issue.SUPPL. D
    • Koser, G.F.1
  • 2
    • 85033148217 scopus 로고
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1990) Synthesis , pp. 431
    • Moriarty, R.M.1    Vaid, R.K.2
  • 3
    • 33748231777 scopus 로고
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 274
    • Stang, P.J.1
  • 4
    • 0003410653 scopus 로고
    • VCH Publishers: New York
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1992) The Organic Chemistry of Polycoordinated Iodine
    • Varvoglis, A.1
  • 5
    • 0345232231 scopus 로고
    • Wiley: New York, Chapter 21
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1995) The Chemistry of Functional Groups , Issue.SUPPL. D2
    • Koser, G.F.1
  • 6
    • 0001213492 scopus 로고    scopus 로고
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1996) Chem. Rev. , vol.96 , pp. 1123
    • Stang, P.J.1    Zhdankin, V.V.2
  • 7
    • 0031502047 scopus 로고    scopus 로고
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1997) Org. Prep. Proc. Int. , vol.29 , pp. 409
    • Kitamura, T.1    Fujiwara, Y.2
  • 8
    • 0004286484 scopus 로고    scopus 로고
    • Akiba, K., Ed.; Wiley-VCH: New York, Chapter 11
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1999) Chemistry of Hypervalent Compounds
    • Zhdankin, V.V.1    Stang, P.J.2
  • 9
    • 0345664278 scopus 로고    scopus 로고
    • Akiba, K., Ed.; Wiley-VCH: New York, Chapter 12
    • For reviews, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 25. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (d) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH Publishers: New York, 1992. (e) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21. (f) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123. (g) Kitamura, T.; Fujiwara, Y. Org. Prep. Proc. Int. 1997, 29, 409. (h) Zhdankin, V. V.; Stang, P. J. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley- VCH: New York, 1999; Chapter 11. (i) Ochiai, M. In Chemistry of Hypervalent Compounds; Akiba, K., Ed.; Wiley-VCH: New York, 1999; Chapter 12.
    • (1999) Chemistry of Hypervalent Compounds
    • Ochiai, M.1
  • 12
    • 0003279562 scopus 로고
    • RN1 mechanism
    • American Chemical Society: Washington, DC
    • RN1 mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983. (b) Aryllead(IV) triacetates: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353. (c) Arylbismuth(V) reagents: Åbramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039. (d) Transition-metalcatalyzed reactions: Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382 and references therein.
    • (1983) ACS Monograph , vol.178
    • Rossi, R.A.1    Rossi, R.H.2
  • 13
    • 84970622394 scopus 로고
    • RN1 mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983. (b) Aryllead(IV) triacetates: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353. (c) Arylbismuth(V) reagents: Åbramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039. (d) Transition-metalcatalyzed reactions: Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382 and references therein.
    • (1991) Aust. J. Chem. , vol.44 , pp. 1353
    • Pinhey, J.T.1
  • 14
    • 40849085240 scopus 로고
    • RN1 mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983. (b) Aryllead(IV) triacetates: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353. (c) Arylbismuth(V) reagents: Åbramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039. (d) Transition-metalcatalyzed reactions: Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382 and references therein.
    • (1988) Tetrahedron , vol.44 , pp. 3039
    • Åbramovitch, R.A.1    Barton, D.H.R.2    Finet, J.-P.3
  • 15
    • 0030664209 scopus 로고    scopus 로고
    • RN1 mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983. (b) Aryllead(IV) triacetates: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353. (c) Arylbismuth(V) reagents: Åbramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039. (d) Transition-metalcatalyzed reactions: Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382 and references therein.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11108
    • Palucki, M.1    Buchwald, S.L.2
  • 16
    • 0000014063 scopus 로고    scopus 로고
    • and references therein
    • RN1 mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983. (b) Aryllead(IV) triacetates: Pinhey, J. T. Aust. J. Chem. 1991, 44, 1353. (c) Arylbismuth(V) reagents: Åbramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039. (d) Transition-metalcatalyzed reactions: Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382 and references therein.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12382
    • Hamann, B.C.1    Hartwig, J.F.2
  • 24
    • 0003078178 scopus 로고
    • 3-iodanes bearing chiral oxygen ligands, see: (a) Imamoto, T.; Koto, H. Chem. Lett. 1986, 967. (b) Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. J. Org. Chem. 1990, 55, 315. (c) Ray, D. G.; Koser, G. F. J. Am. Chem. Soc. 1990, 112, 5672.
    • (1986) Chem. Lett. , pp. 967
    • Imamoto, T.1    Koto, H.2
  • 25
    • 0000229790 scopus 로고
    • 3-iodanes bearing chiral oxygen ligands, see: (a) Imamoto, T.; Koto, H. Chem. Lett. 1986, 967. (b) Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. J. Org. Chem. 1990, 55, 315. (c) Ray, D. G.; Koser, G. F. J. Am. Chem. Soc. 1990, 112, 5672.
    • (1990) J. Org. Chem. , vol.55 , pp. 315
    • Hatzigrigoriou, E.1    Varvoglis, A.2    Bakola-Christianopoulou, M.3
  • 26
    • 0000935985 scopus 로고
    • 3-iodanes bearing chiral oxygen ligands, see: (a) Imamoto, T.; Koto, H. Chem. Lett. 1986, 967. (b) Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. J. Org. Chem. 1990, 55, 315. (c) Ray, D. G.; Koser, G. F. J. Am. Chem. Soc. 1990, 112, 5672.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5672
    • Ray, D.G.1    Koser, G.F.2
  • 27
    • 0000977875 scopus 로고
    • 3-iodanes bearing chiral carbon ligands, see: (a) Ochiai, M.; Takaoka, Y.; Masaki, Y.; Nagao, Y.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 5677. (b) Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453. (c) Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y. J. Am. Chem. Soc. 1997, 119, 619.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5677
    • Ochiai, M.1    Takaoka, Y.2    Masaki, Y.3    Nagao, Y.4    Shiro, M.5
  • 28
    • 0030565520 scopus 로고    scopus 로고
    • 3-iodanes bearing chiral carbon ligands, see: (a) Ochiai, M.; Takaoka, Y.; Masaki, Y.; Nagao, Y.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 5677. (b) Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453. (c) Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y. J. Am. Chem. Soc. 1997, 119, 619.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6453
    • Rabah, G.A.1    Koser, G.F.2
  • 29
    • 0031016214 scopus 로고    scopus 로고
    • 3-iodanes bearing chiral carbon ligands, see: (a) Ochiai, M.; Takaoka, Y.; Masaki, Y.; Nagao, Y.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 5677. (b) Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453. (c) Kitamura, T.; Lee, C. H.; Taniguchi, Y.; Fujiwara, Y. J. Am. Chem. Soc. 1997, 119, 619.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 619
    • Kitamura, T.1    Lee, C.H.2    Taniguchi, Y.3    Fujiwara, Y.4
  • 36
    • 0344801343 scopus 로고    scopus 로고
    • note
    • 13
  • 40
    • 0344801342 scopus 로고    scopus 로고
    • note
    • n. The bond angles C(1)-I-C(21), C(1)-I-F(1), C(21)-I-F(2′), and F(1)-I-F(2′) are 93.8(2), 76.4(2), 100.0(2), and 85.7(2)°, respectively.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.