메뉴 건너뛰기




Volumn , Issue , 2010, Pages 151-169

Asymmetric Phase-Transfer Catalysis for the Production of Non-Proteinogenic α-Amino Acids

Author keywords

Asymmetric alkylation; Chiral quaternary ammonium bromide catalysts; Non proteinogenic amino acids; Phase transfer catalysis

Indexed keywords


EID: 84885792303     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630639.ch9     Document Type: Chapter
Times cited : (5)

References (53)
  • 11
    • 0004232165 scopus 로고    scopus 로고
    • for practical approaches to chiral nonracemic compounds including α-amino acids see: Ager D.(ed.), 2nd edn, CRC Press, Boca Raton, FL
    • for practical approaches to chiral nonracemic compounds including α-amino acids, see: Ager, D. (ed.) (2006) Handbook of Chiral Chemicals, 2nd edn, CRC Press, Boca Raton, FL.
    • (2006) Handbook of Chiral Chemicals
  • 13
    • 70350616302 scopus 로고    scopus 로고
    • (ed. K. Maruoka), Wiley-VCH Verlag GmbH, Weinheim
    • Ooi, T. (2008) in Asymmetric Phase Transfer Catalysis (ed. K. Maruoka), Wiley-VCH Verlag GmbH, Weinheim, pp. 9-33.
    • (2008) In Asymmetric Phase Transfer Catalysis , pp. 9-33
    • Ooi, T.1
  • 18
    • 59349087045 scopus 로고    scopus 로고
    • For application of Cinchona alkaloid-derived phase-transfer catalysts to asymmetric synthesis other than that of α-amino acids see, Wiley-VCH Verlag GmbH, Weinheim, (ed. K. Maruoka)
    • For application of Cinchona alkaloid-derived phase-transfer catalysts to asymmetric synthesis other than that of α-amino acids, see: Arai, S. (2008) in Asymmetric Phase Transfer Catalysis (ed. K. Maruoka), Wiley-VCH Verlag GmbH, Weinheim, pp. 35-48.
    • (2008) In Asymmetric Phase Transfer Catalysis , pp. 35-48
    • Arai, S.1
  • 21
    • 84885759858 scopus 로고    scopus 로고
    • For the disguising immortality of achiral quaternary ammonium salt phase-transfer catalysts see
    • For the disguising immortality of achiral quaternary ammonium salt phase-transfer catalysts, see: Ikunaka, M. (2008) Org. Process Res. Dev., 12, 689-709.
    • (2008) Org. Process Res. Dev. , vol.12 , pp. 689-709
    • Ikunaka, M.1
  • 22
    • 84885727466 scopus 로고    scopus 로고
    • For mechanistic aspects of phase-transfer-catalytic reactions and degenerative fates that quaternary ammonium salts may suffer see, Wiley-VCH Verlag GmbH, Weinheim, (ed. K. Maruoka)
    • For mechanistic aspects of phase-transfer-catalytic reactions and degenerative fates that quaternary ammonium salts may suffer, see: Maruoka, K. (2008) in Asymmetric Phase Transfer Catalysis (ed. K. Maruoka), Wiley-VCH Verlag GmbH, Weinheim, pp. 1-8.
    • (2008) In Asymmetric Phase Transfer Catalysis , pp. 1-8
    • Maruoka, K.1
  • 26
    • 84885720862 scopus 로고    scopus 로고
    • Wiley-VCH Verlag GmbH, Weinheim, (ed. K. Maruoka)
    • Maruoka, K. (2008) in Asymmetric Phase Transfer Catalysis (ed. K. Maruoka), Wiley-VCH Verlag GmbH, Weinheim, pp. 71-113.
    • (2008) In Asymmetric Phase Transfer Catalysis , pp. 71-113
    • Maruoka, K.1
  • 28
    • 84885810850 scopus 로고    scopus 로고
    • 2-symmetric chiral 1,1'-binapthyl-derived quaternary ammonium bromides, such as (S,S)-20, see refs:1a and 18.
  • 32
    • 17144405994 scopus 로고    scopus 로고
    • For asymmetric PTC for the enantioselective alkylation of glycine amide Schiff base see
    • For asymmetric PTC for the enantioselective alkylation of glycine amide Schiff base, see: Ooi, T., Takeuchi, M., Kato, D., Uematsu, Y., Tayama, E., Sakai, D., and Maruoka, K. (2005) J. Am. Chem. Soc., 127, 5073-5083.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 5073-5083
    • Ooi, T.1    Takeuchi, M.2    Kato, D.3    Uematsu, Y.4    Tayama, E.5    Sakai, D.6    Maruoka, K.7
  • 36
    • 84885816944 scopus 로고    scopus 로고
    • For an elaborate yet scalable approach to the eastern azepine-hemisphere of (S,S)- 20, see: (a) ref. 1a.
  • 48
    • 35048842047 scopus 로고    scopus 로고
    • for the selective synthesis of syn-(2R,3S)- 60 see
    • for the selective synthesis of syn-(2R,3S)- 60, see: Ooi, T., Kato, D., Inamura, K., Ohmatsu, K., and Maruoka, K. (2007) Org. Lett., 9, 3945-3948.
    • (2007) Org. Lett. , vol.9 , pp. 3945-3948
    • Ooi, T.1    Kato, D.2    Inamura, K.3    Ohmatsu, K.4    Maruoka, K.5
  • 49
    • 34447272888 scopus 로고    scopus 로고
    • For the latest advances inthe related field see
    • For the latest advances inthe related field, see: (a) Ooi, T. and Maruoka, K. (2007) Angew. Chem. Int. Ed., 46, 4222-4266.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4222-4266
    • Ooi, T.1    Maruoka, K.2
  • 52
    • 84885734691 scopus 로고    scopus 로고
    • 2-symmetric chiral 1,1'-binaphthyl-derived quaternary ammonium salts, such as 20 and 21, and their application to asymmetric PTC for the production of α-amino acid derivatives belong to the proprietary technologies of Nagase & Co., Ltd.: US Patent6 340 753. US Patent 6 441 231. Patent WO 2001/81,349. Patent WO 2005/073196. Patent WO 2006/104,226. these catalysts are collectively named Maruoka Catalyst, a trademark registered by Nagase & Co., Ltd. inJapan,the United States, and major European countries
    • 2-symmetric chiral 1,1'-binaphthyl-derived quaternary ammonium salts, such as 20 and 21, and their application to asymmetric PTC for the production of α-amino acid derivatives belong to the proprietary technologies of Nagase & Co., Ltd.: US Patent6 340 753. US Patent 6 441 231. Patent WO 2001/81,349. Patent WO 2005/073196. Patent WO 2006/104,226. these catalysts are collectively named Maruoka Catalyst, a trademark registered by Nagase & Co., Ltd. inJapan,the United States, and major European countries
  • 53
    • 58149149448 scopus 로고    scopus 로고
    • Special Feature Section: Phase-Transfer Catalysis
    • Special Feature Section: Phase-Transfer Catalysis, (2008) Org. Process Res. Dev., 12, 678-786.
    • (2008) Org. Process Res. Dev. , vol.12 , pp. 678-786


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.