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Volumn 20, Issue 22, 2009, Pages 2600-2608

Resolution of nitrogen-centered chiral tetraalkylammonium salts: application to [1,2] Stevens rearrangements with N-to-C chirality transmission

Author keywords

[No Author keywords available]

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; AMMONIUM DERIVATIVE; MORPHOLINE DERIVATIVE; NITROGEN;

EID: 72049116274     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.025     Document Type: Article
Times cited : (19)

References (33)
  • 1
    • 0000033512 scopus 로고
    • For reviews, see:. Trost B.M., and Fleming I. (Eds), Pergamon, Oxford Chapter 3.10
    • For reviews, see:. Markó I.E. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford 913-974 Chapter 3.10
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 913-974
    • Markó, I.E.1
  • 21
    • 72049120601 scopus 로고    scopus 로고
    • note
    • CCDC-735959 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 22
    • 72049101400 scopus 로고    scopus 로고
    • note
    • 2b); however, the yield and ee of the product 4c were lowered.
  • 23
    • 72049132029 scopus 로고    scopus 로고
    • note
    • 4 reduction and dibenzoylation; this material was then chromatographically correlated with the (S)-authentic sample. The compound (S)-7 was prepared from Schiff-base protected glycine tert-butyl ester via phase transfer catalyzed asymmetric alkylation. Details: see Section 4.2.18.
  • 24
    • 72049086128 scopus 로고    scopus 로고
    • note
    • THF was added as a 1.0 M THF solution of t-BuOK.
  • 25
    • 72049131753 scopus 로고    scopus 로고
    • note
    • 3CN-THF (10:1) at -30 °C for 30 min, (S)-4c was recovered in 74% yield without racemization (60% ee). Use of excess amount of t-BuOK (over 1.0 equiv) in the rearrangement of (R)-1c decreased the chemical yield.
  • 28
    • 72049114361 scopus 로고    scopus 로고
    • note
    • Preparation: Treatment of (R)-1g (80% ee) with (S)-BINOL (1.0 equiv) in dichloromethane afforded the 1:1 complex 2g. Adduct 2g was recrystallized from dichloromethane-hexane; then the crystals were dissociated in diethyl ether-water to give (R)-1g (93% ee).
  • 29
    • 53549085393 scopus 로고    scopus 로고
    • Recently, our group reported that an electron-withdrawing group on N-benzylic substituent enhanced the rate of Sommelet-Hauser rearrangement:
    • Recently, our group reported that an electron-withdrawing group on N-benzylic substituent enhanced the rate of Sommelet-Hauser rearrangement:. Tayama E., Orihara K., and Kimura H. Org. Biomol. Chem. 6 (2008) 3673
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 3673
    • Tayama, E.1    Orihara, K.2    Kimura, H.3
  • 31
    • 72049132818 scopus 로고    scopus 로고
    • note
    • The absolute configurations of 5g and 6g were not determined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.