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Volumn 69, Issue 23, 2004, Pages 8053-8061

PuPHOS: A synthetically useful chiral bidentate ligand for the intermolecular Pauson-Khand reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COBALT; CRYSTALLIZATION; ISOMERIZATION; ISOMERS; MIXTURES; SYNTHESIS (CHEMICAL);

EID: 8744299909     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0486894     Document Type: Article
Times cited : (57)

References (52)
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    • (2004) Chem. Soc. Rev. , vol.33 , pp. 32-42
    • Blanco-Urgoiti, J.1    Anorbe, L.2    Perez-Serrano, L.3    Dominguez, G.4    Perez-Castells, J.5
  • 2
    • 0038665161 scopus 로고    scopus 로고
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1800-1810
    • Gibson, S.E.1    Stevenazzi, A.2
  • 3
    • 0034686072 scopus 로고    scopus 로고
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (2000) Tetrahedron , vol.56 , pp. 3263-3283
    • Brummond, K.M.1    Kent, J.L.2
  • 4
    • 0000939078 scopus 로고    scopus 로고
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (1999) Coord. Chem. Rev. , vol.188 , pp. 297-341
    • Keun Chung, Y.1
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    • 0001216151 scopus 로고    scopus 로고
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (1999) Compr. Asymmetric Catal. , vol.1-3 , pp. 491-510
    • Buchwald, S.L.1    Hicks, F.A.2
  • 6
    • 0001334715 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: Oxford, UK
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037-1064
    • Schore, N.E.1
  • 7
    • 0000939078 scopus 로고    scopus 로고
    • Selected reviews: (a) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32-42. (b) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800-1810. (c) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283. (d) Keun Chung, Y. Coord. Chem. Rev. 1999, 188, 297-341. (d) Buchwald, S. L.; Hicks, F. A. In Compr. Asymmetric Catal. 1999, I-III, pp 491-510. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 1037-1064. (f) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297-341.
    • (1999) Coord. Chem. Rev. , vol.188 , pp. 297-341
    • Chung, Y.K.1
  • 21
    • 0033597871 scopus 로고    scopus 로고
    • Titanium: (a) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547-5550. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rhodium: Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. Iridium: Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853.
    • (1999) J. Org. Chem. , vol.64 , pp. 5547-5550
    • Sturla, S.J.1    Buchwald, S.L.2
  • 22
    • 0033523215 scopus 로고    scopus 로고
    • Titanium: (a) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547-5550. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rhodium: Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. Iridium: Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 7026-7033
    • Hicks, F.A.1    Buchwald, S.L.2
  • 23
    • 0343953463 scopus 로고    scopus 로고
    • Titanium: (a) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547-5550. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rhodium: Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. Iridium: Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6771-6772
    • Jeong, N.1    Sung, B.K.2    Choi, Y.K.3
  • 24
    • 0034638410 scopus 로고    scopus 로고
    • Titanium: (a) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547-5550. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rhodium: Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. Iridium: Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 9852-9853
    • Shibata, T.1    Takagi, K.2
  • 34
    • 8744294157 scopus 로고    scopus 로고
    • note
    • PuPHOS and CyPuPHOS are odorless compounds. Its name derives from the natural compound from which they are synthesized: Pulegone.
  • 39
    • 0003942864 scopus 로고
    • John Wiley & Sons: New York
    • The nomenclature is referred to the cluster terminal carbon atom. According to the alternative prochirality nomenclature in 2D the pro-R (pro-S) ligand would correspond to the Re (Si) ligand, see: Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994.
    • (1994) Stereochemistry of Organic Compounds
    • Eliel, E.L.1    Wilen, S.H.2
  • 40
    • 0038762733 scopus 로고    scopus 로고
    • Wavefunction, Inc.; Irvine, CA
    • Spartan 02; Wavefunction, Inc.; Irvine, CA.
    • Spartan 02
  • 42
    • 8744250565 scopus 로고    scopus 로고
    • note
    • -1 would be necessary at 70°C to attain a 4.5:1 ratio of diastereomers.
  • 44
    • 8744252886 scopus 로고    scopus 로고
    • note
    • Substrate-controlled conjugated addition on 18, removal of TMS fragment, and retro-Diels-Alder reaction will provide chiral cyclopentenones that could formally arise from the aforementioned achiral cyclopentadienone.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.