The aza-Henry reaction of imines with nitromethane was promoted by cinchona alkaloids and modified cinchona bases to give optically active beta-nitroamines. Various N-protected imines were examined as substrates. N-Boc, N-Cbz, and N-Fmoc protected imines gave the best results in terms of chemical yields and enantioselectivities. After a careful screening of a series of chiral bases, very good enantioselectivities up to 94% ee were obtained using a cinchona-based thiourea organocatalyst under the optimized reaction conditions.

Enantioselective aza-Henry reaction using cinchona organocatalysts / Bernardi, Luca; Fini, Francesco; Herrera, Raquel P.; Ricci, Alfredo; Sgarzani, Valentina. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:2-3(2006), pp. 375-380. [10.1016/j.tet.2005.09.076]

Enantioselective aza-Henry reaction using cinchona organocatalysts

FINI, Francesco;
2006

Abstract

The aza-Henry reaction of imines with nitromethane was promoted by cinchona alkaloids and modified cinchona bases to give optically active beta-nitroamines. Various N-protected imines were examined as substrates. N-Boc, N-Cbz, and N-Fmoc protected imines gave the best results in terms of chemical yields and enantioselectivities. After a careful screening of a series of chiral bases, very good enantioselectivities up to 94% ee were obtained using a cinchona-based thiourea organocatalyst under the optimized reaction conditions.
19-ott-2005
62
2-3
375
380
Enantioselective aza-Henry reaction using cinchona organocatalysts / Bernardi, Luca; Fini, Francesco; Herrera, Raquel P.; Ricci, Alfredo; Sgarzani, Valentina. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:2-3(2006), pp. 375-380. [10.1016/j.tet.2005.09.076]
Bernardi, Luca; Fini, Francesco; Herrera, Raquel P.; Ricci, Alfredo; Sgarzani, Valentina
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11380/1122084
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