메뉴 건너뛰기




Volumn 14, Issue 26, 2008, Pages 7951-7960

Stereoselective synthesis of cyclopropanes based on a 1,2-chirality transfer

Author keywords

Asymmetric synthesis; Chirality transfer; Cyclopropanes; Photochemistry; Spin center shift

Indexed keywords

CHIRALITY; ENANTIOMERS; HYDROGEN; PROPANE; STEREOSELECTIVITY;

EID: 53949091618     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801002     Document Type: Article
Times cited : (8)

References (130)
  • 1
    • 0031741997 scopus 로고    scopus 로고
    • and references therein
    • T. Tokoroyama, Chem. Eur. J. 1998, 4, 2397-2404. and references therein.
    • (1998) Chem. Eur. J , vol.4 , pp. 2397-2404
    • Tokoroyama, T.1
  • 4
    • 37049175799 scopus 로고    scopus 로고
    • Original papers: a R. G. W. Norrish, M. E. S. Appleyard, J. Chem. Soc. 1934, 874-880;
    • Original papers: a) R. G. W. Norrish, M. E. S. Appleyard, J. Chem. Soc. 1934, 874-880;
  • 6
    • 33947292229 scopus 로고
    • Selected reviews: A) P.J. Wagner
    • Selected reviews: a) P.J. Wagner, Acc. Chem. Res. 1971, 4, 168-177;
    • (1971) Acc. Chem. Res , vol.4 , pp. 168-177
  • 9
    • 85052764806 scopus 로고
    • Ed, A. Padwa, Marcel Dekker, New York
    • d) P. J. Wagner, B. S. Park, in Organic Photochemistry, Vol. 11 (Ed.: A. Padwa). Marcel Dekker, New York, 1991, p. 227-366;
    • (1991) Organic Photochemistry , vol.11 , pp. 227-366
    • Wagner, P.J.1    Park, B.S.2
  • 10
    • 84964805623 scopus 로고    scopus 로고
    • P. J. Wagner, P. Klán, in Organic Photochemistry and Photobiology. 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 52/1-52/31;
    • e) P. J. Wagner, P. Klán, in Organic Photochemistry and Photobiology. 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 52/1-52/31;
  • 11
    • 85056356739 scopus 로고    scopus 로고
    • T. Hasegawa, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci). CRC Press, Boca Raton, FL, 2003, p. 55/ 1-55/14;
    • f) T. Hasegawa, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci). CRC Press, Boca Raton, FL, 2003, p. 55/ 1-55/14;
  • 12
    • 27444432380 scopus 로고    scopus 로고
    • P. Wessig, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 57/1-57/20;
    • g) P. Wessig, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci), CRC Press, Boca Raton, FL, 2003, p. 57/1-57/20;
  • 13
    • 85056329043 scopus 로고    scopus 로고
    • P. J. Wagner, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci). CRC Press, Boca Raton, FL, 2003, p. 58/1-58/70;
    • h) P. J. Wagner, in Organic Photochemistry and Photobiology, 2nd ed. (Eds.: W. M. Horspool, F. Lenci). CRC Press, Boca Raton, FL, 2003, p. 58/1-58/70;
  • 14
    • 34247244934 scopus 로고    scopus 로고
    • Eds, A. G. Griesbeck, J. Matlay, Marcel Dekker, New York
    • i) P. J. Wagner, in Molecular and Supramolecular Photochemistry, Vol. 12 (Eds.: A. G. Griesbeck, J. Matlay). Marcel Dekker, New York, 2005, p. 11-39;
    • (2005) Molecular and Supramolecular Photochemistry , vol.12 , pp. 11-39
    • Wagner, P.J.1
  • 16
    • 0000984558 scopus 로고    scopus 로고
    • Examples based on simple diastereoselectivity: a A. Azzouzi, M. Dufour, J. C. Gramain, R. Remuson, Heterocyeles 1988, 27, 133-148;
    • Examples based on simple diastereoselectivity: a) A. Azzouzi, M. Dufour, J. C. Gramain, R. Remuson, Heterocyeles 1988, 27, 133-148;
  • 18
    • 53949087708 scopus 로고    scopus 로고
    • Examples based on asymmetric induction via substrate control: a C. Wyss, R. Batra, C. Lehmann, S. Sauer, B. Giese, Angew. Chem. 1996, 108, 2660-2662;
    • Examples based on asymmetric induction via substrate control: a) C. Wyss, R. Batra, C. Lehmann, S. Sauer, B. Giese, Angew. Chem. 1996, 108, 2660-2662;
  • 26
    • 0032845097 scopus 로고    scopus 로고
    • h) P. Wessig, Synlett 1999, 1465-1467;
    • (1999) Synlett , pp. 1465-1467
    • Wessig, P.1
  • 28
    • 0028245244 scopus 로고    scopus 로고
    • Examples based on asymmetric induclion via auxiliary control: a P. Wessig, P. Weltstein, B. Giese, M. Neuburger, M. Zehnder, Helv. Chim. Acta 1994, 77, 829-837;
    • Examples based on asymmetric induclion via auxiliary control: a) P. Wessig, P. Weltstein, B. Giese, M. Neuburger, M. Zehnder, Helv. Chim. Acta 1994, 77, 829-837;
  • 30
    • 0032575148 scopus 로고    scopus 로고
    • Examples based on memory of chirality: a S. Sauer, A. Schumacher, F. Barbosa, B. Giese, Tetrahedron Lett. 1998, 39, 3685-3688;
    • Examples based on memory of chirality: a) S. Sauer, A. Schumacher, F. Barbosa, B. Giese, Tetrahedron Lett. 1998, 39, 3685-3688;
  • 32
    • 0033520303 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 2586-2587;
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 2586-2587
  • 35
    • 18044387608 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2390-2393;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2390-2393
  • 38
    • 0000884192 scopus 로고    scopus 로고
    • and references therein. Review
    • Review: K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074, and references therein.
    • (2000) Chem. Rev , vol.100 , pp. 1025-1074
    • Tanaka, K.1    Toda, F.2
  • 43
    • 0035857554 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1064-1065;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1064-1065
  • 46
    • 0034952305 scopus 로고    scopus 로고
    • For applications of the concept of spin center shift to synthesize oxazinones. benzofuranes and indanones see a
    • For applications of the concept of spin center shift to synthesize oxazinones. benzofuranes and indanones see a) P. Wessig, J. Schwarz, U. Lindemann, M.C. Holthausen, Synthesis 2001, 1258-1262;
    • (2001) Synthesis , pp. 1258-1262
    • Wessig, P.1    Schwarz, J.2    Lindemann, U.3    Holthausen, M.C.4
  • 49
    • 53949097911 scopus 로고    scopus 로고
    • Preliminary communication: P. Wessig, O. Muehling, Angew. Chem. 2005. 117, 6936-6940;
    • Preliminary communication: P. Wessig, O. Muehling, Angew. Chem. 2005. 117, 6936-6940;
  • 50
    • 27444442782 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 6778-6781.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6778-6781
  • 51
    • 53949090909 scopus 로고    scopus 로고
    • This involves SN2′ and SF2′ reactions as well as [2.3, 3,3, 1,5]-sigmatropic rearrangements. Depending on the reaction type a 1,3, 1,4- or 1,5-chirality transfer can be observed. For a detailed examination see R. S. Atkinson, Stereoselective Synthesis, Wiley, Chichester, 1995, Chapter 5, p. 109-146, Chapter 13, p. 381-417, and references therein
    • F2′ reactions as well as [2.3]-. [3,3]-, [1,5]-sigmatropic rearrangements. Depending on the reaction type a 1,3-, 1,4- or 1,5-chirality transfer can be observed. For a detailed examination see R. S. Atkinson, Stereoselective Synthesis, Wiley, Chichester, 1995, Chapter 5, p. 109-146, Chapter 13, p. 381-417, and references therein.
  • 52
    • 53949106855 scopus 로고    scopus 로고
    • Chirality transfer via sigmatropic rearrangements: R. K. Hill, in Asymmetric Synthesis, 3 (Ed.: J. D. Morrison). Academic Press, San Diego, 1984, p. 503-572;
    • a) Chirality transfer via sigmatropic rearrangements: R. K. Hill, in Asymmetric Synthesis, Vol.3 (Ed.: J. D. Morrison). Academic Press, San Diego, 1984, p. 503-572;
  • 53
    • 0038695134 scopus 로고    scopus 로고
    • [3,3]-sigmatropic rearrangements: U. Nubbemeyer, Synthesis 2003, 961-1008;
    • b) [3,3]-sigmatropic rearrangements: U. Nubbemeyer, Synthesis 2003, 961-1008;
  • 54
    • 53949114954 scopus 로고    scopus 로고
    • [3,3]-sigmatropic rearrangements: H. Frauenrath, in Methods of Organic Chemistry, E21 (Houben Weyl), Thieme, Stuttgart, 1995, p. 3301-3756;
    • c) [3,3]-sigmatropic rearrangements: H. Frauenrath, in Methods of Organic Chemistry, Vol. E21 (Houben Weyl), Thieme, Stuttgart, 1995, p. 3301-3756;
  • 55
    • 53949114334 scopus 로고    scopus 로고
    • [2,3]sigmatropic rearrangements: J. Kallmerten, in Methods of Organic Chemistry, E21 (Houben Weyl), Thieme, Stuttgart, 1995, p. 3757-3809;
    • d) [2,3]sigmatropic rearrangements: J. Kallmerten, in Methods of Organic Chemistry, Vol. E21 (Houben Weyl), Thieme, Stuttgart, 1995, p. 3757-3809;
  • 56
    • 53949088337 scopus 로고    scopus 로고
    • Wittig rearrangements: T. Nakai, K. Mikami, Org. React. 1994, 46, 105-209;
    • e) Wittig rearrangements: T. Nakai, K. Mikami, Org. React. 1994, 46, 105-209;
  • 57
    • 53949100541 scopus 로고    scopus 로고
    • copper-mediated allylic substitution: B. Breit, P. Demel, C. Studte, Angew. Chem. 2004, 116, 3874-3877;
    • f) copper-mediated allylic substitution: B. Breit, P. Demel, C. Studte, Angew. Chem. 2004, 116, 3874-3877;
  • 58
    • 4544273059 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2004, 43, 3786-3789, and references therein.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3786-3789
  • 59
    • 0000204989 scopus 로고    scopus 로고
    • A CAS search for the keyword 1,2-chirality transfer provided only two references: a W. Smadja, S. Czernecki, G. Ville, C. Georgoulis, Organometallics 1987, 6, 166-169;
    • A CAS search for the keyword "1,2-chirality transfer" provided only two references: a) W. Smadja, S. Czernecki, G. Ville, C. Georgoulis, Organometallics 1987, 6, 166-169;
  • 61
    • 53949109951 scopus 로고    scopus 로고
    • Comprehensive review about the α-hydroxylation of enolates and silyl enolethers: B.-C. Chen, P. Zhou, F. A. Davis, E. Ciganek, Org. React. 2003, 62, 1-356, and references therein;
    • a) Comprehensive review about the α-hydroxylation of enolates and silyl enolethers: B.-C. Chen, P. Zhou, F. A. Davis, E. Ciganek, Org. React. 2003, 62, 1-356, and references therein;
  • 62
    • 53949118304 scopus 로고    scopus 로고
    • Short review concerning the preparation of α-hydroxy carbonyl compounds by organocatalytic α-aminoxylation: P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058;
    • b) Short review concerning the preparation of α-hydroxy carbonyl compounds by organocatalytic α-aminoxylation: P. Merino, T. Tejero, Angew. Chem. 2004, 116, 3055-3058;
  • 63
    • 4344651796 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2995-2997.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 2995-2997
  • 72
    • 84987537488 scopus 로고    scopus 로고
    • Two-step synthesis of 9 from benzaldehyde: D. Burkhouse, H. Zimmer, Synthesis 1984, 330-332.
    • Two-step synthesis of 9 from benzaldehyde: D. Burkhouse, H. Zimmer, Synthesis 1984, 330-332.
  • 73
    • 53949102574 scopus 로고    scopus 로고
    • 4] (0.2 mol%), see also ref. [20].
    • 4] (0.2 mol%), see also ref. [20].
  • 88
  • 89
    • 0034696113 scopus 로고    scopus 로고
    • 0 as equipodal temperature: Y. Inoue, T. Wada, S. Asaoka, H. Sato, J.-P. Pète, Chem. Commun. 2000, 251-259;
    • 0 as "equipodal temperature": Y. Inoue, T. Wada, S. Asaoka, H. Sato, J.-P. Pète, Chem. Commun. 2000, 251-259;
  • 90
    • 0033531612 scopus 로고    scopus 로고
    • Cainelli chose the term equiseleclive temperature: G. Cainelli, D. Giacomini, P. Galletti, Chem. Commun. 1999, 567-572.
    • b) Cainelli chose the term "equiseleclive temperature": G. Cainelli, D. Giacomini, P. Galletti, Chem. Commun. 1999, 567-572.
  • 91
    • 37049129164 scopus 로고    scopus 로고
    • 0: a K. Harada, T. Yoshida, J. Chem. Soc. Chem. Commun. 1970, 1071;
    • 0: a) K. Harada, T. Yoshida, J. Chem. Soc. Chem. Commun. 1970, 1071;
  • 95
    • 0034603102 scopus 로고    scopus 로고
    • and references therein;
    • Angew. Chem. Int. Ed. 2000, 39, 523-527, and references therein;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 523-527
  • 97
    • 4344561898 scopus 로고    scopus 로고
    • 0: a T. Poon, J. Sivaguru, R. Franz, S. Jockusch, C. Martinez, I. Washington, W. Adam, Y. Inoue, N. J. Turro, J. Am. Chem. Soc. 2004, 126, 10498-10499;
    • 0: a) T. Poon, J. Sivaguru, R. Franz, S. Jockusch, C. Martinez, I. Washington, W. Adam, Y. Inoue, N. J. Turro, J. Am. Chem. Soc. 2004, 126, 10498-10499;
  • 100
    • 0037051959 scopus 로고    scopus 로고
    • and references therein;
    • d) W. Adam, V. R. Stegmann, J. Am. Chem. Soc. 2002, 124, 3600-3607, and references therein;
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 3600-3607
    • Adam, W.1    Stegmann, V.R.2
  • 104
    • 1842368466 scopus 로고    scopus 로고
    • Reactions without selectivity reversal in the investigated temperature region, but with an entropy controlled increase of selectivity with increasing temperature: a T. Bach, K. Jödicke, K. Kather, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 2437-2445;
    • Reactions without selectivity reversal in the investigated temperature region, but with an entropy controlled increase of selectivity with increasing temperature: a) T. Bach, K. Jödicke, K. Kather, R. Fröhlich, J. Am. Chem. Soc. 1997, 119, 2437-2445;
  • 111
    • 33646507198 scopus 로고    scopus 로고
    • For the purpose of completeness and to avoid confusions a second type of selectivity reversal should be pointed out shortly. In the case of a non-linear correlation between selectivity and 1/T, the corresponding Eyring plots generally consist of two (nearly) linear regions intersecting at an extremum, the inversion point. Both linear regions are characterized by their own set of activation parameters. In contrast to a selectivity reversal at T 0 (S=0, here the selectivity S reaches a (local) minimum or maximum at the inversion temperature (Tinv, According to the isoinversion principle of Scharf [a) H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath. J. Runsink, J. Am. Chem. Soc. 1989, 111, 5367-5373;
    • inv). According to the isoinversion principle of Scharf [a) H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath. J. Runsink, J. Am. Chem. Soc. 1989, 111, 5367-5373;
  • 113
    • 0025780257 scopus 로고    scopus 로고
    • inv the dominance of ΔΔH* and ΔΔS* changes in the corresponding selectivity level. However, the discussion on the nature of inversion points is still open
    • inv the dominance of ΔΔH* and ΔΔS* changes in the corresponding selectivity level. However, the discussion on the nature of inversion points is still open
  • 124
    • 53949118851 scopus 로고    scopus 로고
    • Gaussian 98 Revision A9, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanos G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc, Pittsburgh, PA, 1998
    • Gaussian 98 (Revision A9). M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanos G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.