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Volumn 74, Issue 16, 2009, Pages 6319-6322

Lithiation of N-alkyl-(o-tolyl)aziridine: Stereoselective synthesis of isochromans

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE RING; AZIRIDINES; CHEMICAL EQUATIONS; ELECTROPHILES; FUNCTIONALIZED; LITHIATION; LITHIATION REACTION; METALATIONS; STEREOSELECTIVE PREPARATION; STEREOSELECTIVE SYNTHESIS;

EID: 70349115204     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9011943     Document Type: Article
Times cited : (39)

References (50)
  • 2
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    • Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, UK
    • (b) Padwa, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier: Oxford, UK, 2008; Vol.1, pp 1-104.
    • (2008) Comprehensive Heterocyclic Chemistry III , vol.1 , pp. 1-104
    • Padwa, A.1
  • 4
    • 1542375289 scopus 로고    scopus 로고
    • (d) Hu, X. E. Tetrahedron 2004, 60, 2701-2743.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 28
    • 0003961355 scopus 로고    scopus 로고
    • It is likely that the nitrogen-induced stabilization in the six-membered cyclic lithiated intermediated 1-Li, and Complex Induced Proximity Effect could act sinergically making the lateral benzylic position the kinetically and thermodynamically favored one, see: (a) Pergamon: Oxford, UK, Chapter 2
    • It is likely that the nitrogen-induced stabilization in the six-membered cyclic lithiated intermediated 1-Li, and Complex Induced Proximity Effect could act sinergically making the lateral benzylic position the kinetically and thermodynamically favored one, see: (a) Clayden J., In Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, UK, 2002; Chapter 2.
    • (2002) Organolithiums: Selectivity for Synthesis
    • Clayden, J.1
  • 30
    • 0037023420 scopus 로고    scopus 로고
    • For other examples of nitrogen-assisted lithiation see: (a)
    • For other examples of nitrogen-assisted lithiation see: (a) Ross Kelly, T.; Lebedev, R. L. J. Org. Chem. 2002, 67, 2197-2205.
    • (2002) J. Org. Chem. , vol.67 , pp. 2197-2205
    • Ross Kelly, T.1    Lebedev, R.L.2
  • 37
    • 70349159807 scopus 로고    scopus 로고
    • note
    • Following a referee's suggestion, the one-pot cyclization was performed by addition of 2 mL of acetic acid to the reaction mixture (1 mmol scale) obtained after quenching of the lithiated intermediate with benzophenone. The complete conversion of 2f into 3b was observed and the isochroman was isolated with 40% yield.
  • 39
    • 70349117165 scopus 로고    scopus 로고
    • note
    • This assumption rises considering that the reaction on pure diastereomers of (R*,R*)-2h,i and (R*,S*)-2h,i is highly stereospecific giving only one isochroman. Likely, a mixture of diastereomeric isochromans should have been obtained with an SN1 mechanism.
  • 40
    • 70349156120 scopus 로고    scopus 로고
    • note
    • 3COOH to the starting aziridine 2.
  • 41
    • 70349159350 scopus 로고    scopus 로고
    • CCDC 733354 contains the supplementary crystallographic data for compound (R*,R*)-2i. These data have been deposited with the Cambridge Crystallographic Data Centre and can be obtained free of charge via
    • CCDC 733354 contains the supplementary crystallographic data for compound (R*,R*)-2i. These data have been deposited with the Cambridge Crystallographic Data Centre and can be obtained free of charge via www. ccdc.cam.ac.uk/data-request/cif.
  • 47
    • 0002994828 scopus 로고
    • The resonance effect is often invoked for this kind of intermediate even if their structures are still unknown, see: (a)
    • The resonance effect is often invoked for this kind of intermediate even if their structures are still unknown, see: (a) Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1-314.
    • (1995) Org. React. , vol.47 , pp. 1-314
    • Clark, R.D.1    Jahangir, A.2
  • 49
    • 42149123402 scopus 로고    scopus 로고
    • A NMR investigation could help to shed light on this isomerization process; for a related example on the solvent effect, see
    • A NMR investigation could help to shed light on this isomerization process; for a related example on the solvent effect, see: Capriati, V.; Florio, S.; Luisi, R.; Mazzanti, A.; Musio, B. J. Org. Chem. 2008, 73, 3197-3204.
    • (2008) J. Org. Chem. , vol.73 , pp. 3197-3204
    • Capriati, V.1    Florio, S.2    Luisi, R.3    Mazzanti, A.4    Musio, B.5
  • 50
    • 70349090376 scopus 로고    scopus 로고
    • note
    • The absolute configuration could be assigned considering that the intramolecular cyclization is highly stereospecific (see infra).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.