Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate

Stoncius A, Mast CA, Sewald N (2000)
TETRAHEDRON-ASYMMETRY 11(19): 3849-3853.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
The conjugate addition of methylcuprates and methyllithium to ethyl 5-phenyl-1,3-dioxolan-4-yl-2-propenoate was investigated. It was found that the stereoselectivity is highly dependent on the reagent used. In reactions with stabilized methylcuprates, the anti-1,4-addition product is mainly formed, whereas syn-diastereoselectivity is observed in the reaction with methyllithium. Additions of methyllithium were optimized with respect to solvent and additives. (C) 2000 Elsevier Science Ltd. All rights reserved.
Erscheinungsjahr
Zeitschriftentitel
TETRAHEDRON-ASYMMETRY
Band
11
Zeitschriftennummer
19
Seite
3849-3853
ISSN
PUB-ID

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Stoncius A, Mast CA, Sewald N. Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate. TETRAHEDRON-ASYMMETRY. 2000;11(19):3849-3853.
Stoncius, A., Mast, C. A., & Sewald, N. (2000). Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate. TETRAHEDRON-ASYMMETRY, 11(19), 3849-3853. doi:10.1016/S0957-4166(00)00353-0
Stoncius, A., Mast, C. A., and Sewald, N. (2000). Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate. TETRAHEDRON-ASYMMETRY 11, 3849-3853.
Stoncius, A., Mast, C.A., & Sewald, N., 2000. Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate. TETRAHEDRON-ASYMMETRY, 11(19), p 3849-3853.
A. Stoncius, C.A. Mast, and N. Sewald, “Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate”, TETRAHEDRON-ASYMMETRY, vol. 11, 2000, pp. 3849-3853.
Stoncius, A., Mast, C.A., Sewald, N.: Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate. TETRAHEDRON-ASYMMETRY. 11, 3849-3853 (2000).
Stoncius, A, Mast, CA, and Sewald, Norbert. “Control of diastereofacial discrimination in the conjugate addition to 5-phenyl-1,3-dioxolan-4-yl substituted propenoate”. TETRAHEDRON-ASYMMETRY 11.19 (2000): 3849-3853.