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Volumn , Issue 4, 2011, Pages 543-546

Asymmetric carbonyl migration of α-amino acid derivatives via memory of chirality

Author keywords

amino acids; carbonyl migration; chirality; stereoselectivity; tetrasubstituted carbon

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; AMINO ACID DERIVATIVE; CARBONYL DERIVATIVE; LITHIUM 2.2,6.6 TETRAMETHYLPIPERIDIDE; LITHIUM HEXAMETHYLDISILAZIDE; POTASSIUM HEXAMETHYLDISILAZIDE; SODIUM HEXAMETHYLDISILAZIDE; UNCLASSIFIED DRUG;

EID: 79951857007     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259324     Document Type: Article
Times cited : (10)

References (21)
  • 1
    • 0345022255 scopus 로고
    • For asymmetric intermolecular alkylation via memory of chirality, see: (a)
    • For asymmetric intermolecular alkylation via memory of chirality, see: (a) Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9694
    • Kawabata, T.1    Yahiro, K.2    Fuji, K.3
  • 4
    • 0142245598 scopus 로고    scopus 로고
    • For asymmetric intramolecular alkylation via memory of chirality, see: (a)
    • For asymmetric intramolecular alkylation via memory of chirality, see: (a) Kawabata, T.; Kawakami, S.; Majumdar, S. J. Am. Chem. Soc. 2003, 125, 13012.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13012
    • Kawabata, T.1    Kawakami, S.2    Majumdar, S.3
  • 7
    • 18844438937 scopus 로고    scopus 로고
    • For asymmetric intramolecular conjugate addition via memory of chirality, see
    • For asymmetric intramolecular conjugate addition via memory of chirality, see: Kawabata, T.; Majuumdar, S.; Tsubaki, K.; Monguchi, D. Org. Biomol. Chem. 2005, 3, 1609.
    • (2005) Org. Biomol. Chem. , vol.3 , pp. 1609
    • Kawabata, T.1    Majuumdar, S.2    Tsubaki, K.3    Monguchi, D.4
  • 8
    • 61349145077 scopus 로고    scopus 로고
    • For Dieckmann condensation via memory of chirality, see
    • For Dieckmann condensation via memory of chirality, see: Watanabe, T.; Kawabata, T. Heterocycles 2008, 76, 1593.
    • (2008) Heterocycles , vol.76 , pp. 1593
    • Watanabe, T.1    Kawabata, T.2
  • 9
    • 0042929265 scopus 로고    scopus 로고
    • For recent reviews on asymmetric synthesis via memory of chirality see: (a)
    • For recent reviews on asymmetric synthesis via memory of chirality see: (a) Kawabata, T.; Fuji, K. Top. Stereochem. 2003, 53, 175.
    • (2003) Top. Stereochem. , vol.53 , pp. 175
    • Kawabata, T.1    Fuji, K.2
  • 11
    • 84897983914 scopus 로고    scopus 로고
    • Asymmetric Synthesis and Application of α-Amino Acids
    • American Chemical Society: Washington DC
    • (c) Kawabata, T. Asymmetric Synthesis and Application of α-Amino Acids, ACS Symposium Series 1009; American Chemical Society: Washington DC, 2009, 31-56.
    • (2009) ACS Symposium Series 1009 , pp. 31-56
    • Kawabata, T.1
  • 14
    • 79951854184 scopus 로고    scopus 로고
    • note
    • The most stable conformer B was generated by a molecular modeling search (MCMM 50,000 steps) with OPLS 2005 force field and GB/SA solvation model for chloroform using MacroModel (V. 9.0); see Supporting Information.
  • 15
    • 79951857359 scopus 로고    scopus 로고
    • note
    • Ei process. This route was excluded by the experimental results in the case of asymmetric cyclization shown in Scheme 5 (refs. 2a and 2c). By analogy, we assume that the present asymmetric carbonyl migration would proceed through an axially chiral enolate intermediate.
  • 21
    • 79951855289 scopus 로고    scopus 로고
    • note
    • 4Na: 418.1994; found: 418.1953.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.