메뉴 건너뛰기




Volumn 3, Issue 1, 2008, Pages 137-143

Synthesis of enantiomerically enriched (R)-5-tert-butylazepan-2-one using a hydroxyalkyl azide mediated ring-expansion reaction

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 3 AZIDOPROPANOL; 3 AZIDO 1 PHENYLPROPAN 1 OL; 5 TERT BUTYL 1 (3 HYDROXY 3 PHENYLPROPYL)AZEPAN 2 ONE; 5 TERT BUTYL 1 (3 OXO 3 PHENYLPROPYL)AZEPAN 2 ONE; 5 TERT BUTYLAZEPAN 2 ONE; AZIDE; AZIDO 1 PHENYLPROPANOL; CAPROLACTAM; HYDROXYALKYLAZIDE; KETONE DERIVATIVE; LEWIS ACID; PROPANOL; UNCLASSIFIED DRUG;

EID: 38349117502     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2007.518     Document Type: Article
Times cited : (4)

References (14)
  • 1
    • 0006077638 scopus 로고    scopus 로고
    • Synthesis of medium-sized ring lactams
    • Nubbemeyer, U. Synthesis of medium-sized ring lactams. Top. Curr. Chem. 216, 125-196 (2001).
    • (2001) Top. Curr. Chem , vol.216 , pp. 125-196
    • Nubbemeyer, U.1
  • 2
    • 0026093828 scopus 로고
    • Medium ring nitrogen heterocycles
    • Evans, P.A. & Holmes, A.B. Medium ring nitrogen heterocycles. Tetrahedron 47, 9131-9166 (1991).
    • (1991) Tetrahedron , vol.47 , pp. 9131-9166
    • Evans, P.A.1    Holmes, A.B.2
  • 4
    • 0031047517 scopus 로고    scopus 로고
    • Chiral bicyclic lactams: Useful precursors and templates for asymmetric syntheses
    • Meyers, A.I. &, Brengel, G.P. Chiral bicyclic lactams: Useful precursors and templates for asymmetric syntheses. J. Chem. Soc. Chem. Commun. 1-8 (1997).
    • (1997) J. Chem. Soc. Chem. Commun , vol.1-8
    • Meyers, A.I.1    Brengel, G.P.2
  • 5
    • 33751205329 scopus 로고    scopus 로고
    • Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis
    • Arisawa, M., Nishida, A. & Nakagawa, M. Preparation of nitrogen-containing heterocycles using ring-closing metathesis (RCM) and its application to natural product synthesis. J. Organomet. Chem. 691, 5109-5121 (2006).
    • (2006) J. Organomet. Chem , vol.691 , pp. 5109-5121
    • Arisawa, M.1    Nishida, A.2    Nakagawa, M.3
  • 6
    • 0035917345 scopus 로고    scopus 로고
    • Effect of progressive benzyl substitution on the conformations of aminocaproic acid-cyclized dipeptides
    • MacDonald, M., Vander Velde, D. & Aubé, J. Effect of progressive benzyl substitution on the conformations of aminocaproic acid-cyclized dipeptides. J. Org. Chem. 66, 2636-2642 (2001).
    • (2001) J. Org. Chem , vol.66 , pp. 2636-2642
    • MacDonald, M.1    Vander Velde, D.2    Aubé, J.3
  • 7
    • 1442299909 scopus 로고    scopus 로고
    • Synthesis and conformational studies of dipeptides constrained by disubstituted 3-(aminoethoxy)propionic acid linkers
    • Reddy, D.S., Vander Velde, D. & Aube, J. Synthesis and conformational studies of dipeptides constrained by disubstituted 3-(aminoethoxy)propionic acid linkers. J. Org. Chem. 69, 1716-1719 (2004).
    • (2004) J. Org. Chem , vol.69 , pp. 1716-1719
    • Reddy, D.S.1    Vander Velde, D.2    Aube, J.3
  • 8
    • 33846283043 scopus 로고    scopus 로고
    • Oxaziridine rearrangements in asymmetric synthesis
    • Aubé, J. Oxaziridine rearrangements in asymmetric synthesis. Chem. Soc. Rev. 26, 269-277 (1997).
    • (1997) Chem. Soc. Rev , vol.26 , pp. 269-277
    • Aubé, J.1
  • 9
    • 0005694590 scopus 로고
    • Efficient nitrogen ring-expansion process facilitated by in situ hemiketal formation. An asymmetric Schmidt reaction
    • Gracias, V., Milligan, G.L. & Aubé, J. Efficient nitrogen ring-expansion process facilitated by in situ hemiketal formation. An asymmetric Schmidt reaction. J. Am. Chem. Soc. 117, 8047-8048 (1995).
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 8047-8048
    • Gracias, V.1    Milligan, G.L.2    Aubé, J.3
  • 10
    • 0033549679 scopus 로고    scopus 로고
    • 1,7-Asymmetric induction in a nitrogen ring expansion process facilitated by in situ tethering
    • Furness, K. & Aubé, J. 1,7-Asymmetric induction in a nitrogen ring expansion process facilitated by in situ tethering. Org. Lett. 1, 495-497 (1999).
    • (1999) Org. Lett , vol.1 , pp. 495-497
    • Furness, K.1    Aubé, J.2
  • 11
    • 0038540861 scopus 로고    scopus 로고
    • Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones
    • Sahasrabudhe, K. et al.. Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones. J. Am. Chem. Soc. 125, 7914-7922 (2003).
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 7914-7922
    • Sahasrabudhe, K.1
  • 12
    • 36649013845 scopus 로고    scopus 로고
    • Molecular building kit of fused-proline-derived peptide mimetics allowing specific adjustment of the dihedral psi angle
    • Einsiedel, J., Lanig, H., Waibel, R. & Gmeiner, P. Molecular building kit of fused-proline-derived peptide mimetics allowing specific adjustment of the dihedral psi angle. J. Org. Chem. 72, 9102-9113 (2007).
    • (2007) J. Org. Chem , vol.72 , pp. 9102-9113
    • Einsiedel, J.1    Lanig, H.2    Waibel, R.3    Gmeiner, P.4
  • 13
    • 36849027181 scopus 로고    scopus 로고
    • Concise constructiorl of novel bridged bicyclic lactams by sequenced Ugi/RCM/Heck reactions
    • Ribelin, T.P. et al.. Concise constructiorl of novel bridged bicyclic lactams by sequenced Ugi/RCM/Heck reactions. Org. Lett. 9, 5119-5122 (2007).
    • (2007) Org. Lett , vol.9 , pp. 5119-5122
    • Ribelin, T.P.1
  • 14
    • 0025031913 scopus 로고
    • Synthetic aspects of an asymmetric nitrogen-insertion process: Preparation of chiral, non-racemic caprolactams and valerolactams. Total synthesis of (-)-alloyohimpbane
    • Aubé, J. et al.. Synthetic aspects of an asymmetric nitrogen-insertion process: Preparation of chiral, non-racemic caprolactams and valerolactams. Total synthesis of (-)-alloyohimpbane. J. Am. Chem. Soc. 112, 4879-4891 (1990).
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 4879-4891
    • Aubé, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.