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Abstract:

Addition of butyl- and phenyllithium to α-thujone (1) and to β-thujone (2) has been studied. The reaction produces optically active tertiary alcohols useful for the preparation of several intermediates in the synthesis of chiral compounds. The present highly strained ketones are also suitable to study the stereochemistry of addition; some torsional strain to attack by BuLi from the-side is shown by 1 (ca. 76% α vs. 24% β), while 2 produces only the 3-butylneoisothujol as a result of addition from the α-face. A surprising exclusive attack from the β-face is exerted by PhLi; a hypothesis based on a late transition state is proposed to explain the observed anomaly. © 1984, American Chemical Society. All rights reserved.

Registro:

Documento: Artículo
Título:Addition of Butyl- and Phenyllithium to Thujones
Autor:Sbarbati Nudelman, N.; Gatto, Z.; Bohé, L.
Filiación:Departamento de QuÍmica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, United States
Instituto de Investigaciones de Productos Naturales, Análisis y Síntesis Orgánica, IPNAYS (CONICET-UNL-FIQ), Santiago del Estero 2829, 3000 Santa Fe, United States
Año:1984
Volumen:49
Número:9
Página de inicio:1540
Página de fin:1544
DOI: http://dx.doi.org/10.1021/jo00183a013
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v49_n9_p1540_SbarbatiNudelman

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Citas:

---------- APA ----------
Sbarbati Nudelman, N., Gatto, Z. & Bohé, L. (1984) . Addition of Butyl- and Phenyllithium to Thujones. Journal of Organic Chemistry, 49(9), 1540-1544.
http://dx.doi.org/10.1021/jo00183a013
---------- CHICAGO ----------
Sbarbati Nudelman, N., Gatto, Z., Bohé, L. "Addition of Butyl- and Phenyllithium to Thujones" . Journal of Organic Chemistry 49, no. 9 (1984) : 1540-1544.
http://dx.doi.org/10.1021/jo00183a013
---------- MLA ----------
Sbarbati Nudelman, N., Gatto, Z., Bohé, L. "Addition of Butyl- and Phenyllithium to Thujones" . Journal of Organic Chemistry, vol. 49, no. 9, 1984, pp. 1540-1544.
http://dx.doi.org/10.1021/jo00183a013
---------- VANCOUVER ----------
Sbarbati Nudelman, N., Gatto, Z., Bohé, L. Addition of Butyl- and Phenyllithium to Thujones. J. Org. Chem. 1984;49(9):1540-1544.
http://dx.doi.org/10.1021/jo00183a013