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Tetrahedron Asymmetry

Volumn 11, Issue 19, 2000, Pages 3845-3848

The regio- and stereoselective oxyamination of pinenes and camphene

(5) Pinheiro, Sergio a Pedraza, Sérgio F a Farias, Florence M C a Gonçalves, Angelo S b Costa, Paulo R R b

a FLUMINENSE FEDERAL UNIVERSITY (Brazil)

b Laboratório de Química Bioorgânica Núcleo de Pesquisas de Produtos Naturais Centro de Ciências da Saúde (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BETA AMINOALKANOL; CAMPHENE DERIVATIVE; PINENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034612958 PISSN: 09574166 EISSN: None Source Type: Journal
DOI: 10.1016/S0957-4166(00)00382-7 Document Type: Article

Times cited : (6)

References (21)

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15
- 0007451956
- (1S)-(-)-α-Pinene (81% e.e.), (1S)-(-)-β-pinene (97% e.e.), (-)-camphene, (1R)-(-)-nopol and (1R)-(-)-nopol benzyl ether were purchased from Aldrich Chem. Co.

16
- 0007383294
- 3); 28.0 (t, C7); 27.7 (q, C9); 24.1 (q, C8).

17
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- Analytical and spectral data are in agreement with the literature. See Ref. 14d.

18
- 0007425334
- 13b is expected to give (1R,2R,3S,5R)-3-amino-2-hydroxypinane, which is an effective chiral ligand for borane reductions of aryl ketones and α-oxoketoxime trityl ethers: (a) Masui, M.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5195. (b) Masui, M.; Shioiri, T. Tetrahedron Lett. 1998, 39, 5199. (c) Masui, M.; Shioiri, T. Synlett 1997, 273. (d) Masui, M.; Shioiri, T. Synlett 1996, 49.

19
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- 3); 26.6 (t, C3); 24.6 (t, C4); 22.9 (q, C9); 21.4 (q, C8).

20
- 0007379803
- 3); 23.3 (t, C5); 22.7 (t, C4); 21.8 (q, C9); 21.4 (q, C8).

21
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- (1989) J. Org. Chem. , vol.54 , pp. 1764
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