Symmetrical 4,4′,6,6′-tetraarylbinaphthyl-substituted ammonium bromide as a new, chiral phase-transfer catalyst

Tetrahedron Asymmetry

Volumn 14, Issue 12, 2003, Pages 1599-1602

  Hashimoto, Takuya ^a   Tanaka, Youhei ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; BROMINE DERIVATIVE; GLYCINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; PHASE TRANSITION; PRIORITY JOURNAL;

EID: 0037867763     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00271-4     Document Type: Article

References (23)

1. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
2. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
3. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
4. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
5. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
6. For recent reviews on chiral phase-transfer catalysis, see: (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Verlag Chemie: New York, 1993; Chapter 8; (b) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14; (c) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1998, Issue 4, p. 5; (d) O'Donnell, M. J. Phases - The Sachem Phase Transfer Catalysis Review 1999, Issue 5, p. 5; (e) Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123; (f) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3.
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16. Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc., in press.
17. 2-symmetric guanidine based and tartrate-derived chiral phase-transfer catalysts have been developed. See: (a) Kita, T.; Georgieva, A.; Hashimoto, U.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832; (b) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535; (c) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539.
18. 2-symmetric guanidine based and tartrate-derived chiral phase-transfer catalysts have been developed. See: (a) Kita, T.; Georgieva, A.; Hashimoto, U.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832; (b) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535; (c) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539.
19. 2-symmetric guanidine based and tartrate-derived chiral phase-transfer catalysts have been developed. See: (a) Kita, T.; Georgieva, A.; Hashimoto, U.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832; (b) Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535; (c) Shibuguchi, T.; Fukuta, Y.; Akachi, Y.; Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 9539.
20. Gong L.-Z., Hu Q.-S., Pu L. J. Org. Chem. 66:2001;2358.
21. Cui Y., Evans O.R., Ngo H.L., White P.S., Lin W. Angew. Chem., Int. Ed. 41:2002;1159.
22. The catalyst 3a was recovered in ∼50% yield, suggesting the partial decomposition of 3a under the phase-transfer conditions. In contrast, catalyst 1 having 3,3-diaryl substituents is stable and gives higher recovery yield than 3. See Ref. 2c.
23. Because of the difficulty for 4,4′,6,6′-tetrakis(3,5-diphenylphenyl)binaphthyl analogue in radical bromination as shown in Scheme 2, we developed a new synthetic route to 4c as indicated in Scheme 4.