Zinc(ii) ortho-hydroxyphenylhydrazo-β-diketonate complexes and their catalytic ability towards diastereoselective nitroaldol (Henry) reaction

Kopylovich M.N.; Mac Leod T.C.O.; Mahmudov K.T.; Guedes Da Silva M.F.C.; Pombeiro A.J.L.

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Zinc(ii) ortho-hydroxyphenylhydrazo-β-diketonate complexes and their catalytic ability towards diastereoselective nitroaldol (Henry) reaction

机译：邻位羟基苯基肼-β-二酮酸锌（ii）配合物对非对映选择性硝基羟醛（Henry）反应的催化能力

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The zinc(ii) complexes with ortho-hydroxy substituted arylhydrazo-β- diketonates [Zn_2(CH_3OH)_2(μ-L ~1)_2] (5), [Zn{(CH_3)_2SO}(H _2O)(L~2)] (6), [Zn_2(H_2O) _2(μ-L~3)_2] (7) and [Zn(H_2O) _2(L~4)]·H_2O (8) were synthesized by reaction of a zinc(ii) salt with the appropriate hydrazo-β-diketone, HO-2-C_6H_4-NHNC{C(O)CH_3}_2 (H _2L~1, 1), HO-2-O_2N-4-C_6H _3-NHNC{C(O)CH_3}_2 (H_2L~2, 2), HO-2-C_6H_4-NHNCC(O)CH_2C(CH_3) _2CH_2C(O) (H_2L~3, 3) or HO-2-O _2N-4-C_6H_3-NHNCC(O)CH_2C(CH _3)_2CH_2C(O) (H_2L~4, 4). They were fully characterized, namely by X-ray diffraction analysis that disclosed the formation of extensive H-bonds leading to 1D chains (5 and 6), 2D layers (7) or 3D networks (8). The thermodynamic parameters of the Zn(ii) reaction with H_2L~2 in solution, as well as of the thermal decomposition of 1-8 were determined. Complexes 5-8 act as diastereoselective catalysts for the nitroaldol (Henry) reaction. The threo/erythro diastereoselectivity of the β-nitroalkanol products ranges from 8:1 to 1:10 with typical yields of 80-99%, depending on the catalyst and substrate used.

机译：锌（ii）与邻羟基取代的芳基偶氮-β-二酮酸酯[Zn_2（CH_3OH）_2（μ-L〜1）_2]（5），[Zn {（CH_3）_2SO}（H _2O）（L〜 2）]（6），通过锌反应合成[Zn_2（H_2O）_2（μ-L〜3）_2]（7）和[Zn（H_2O）_2（L〜4）]·H_2O（8）。（ii）与适当的肼基-β-二酮，HO-2-C_6H_4-NHNC {C（O）CH_3} _2（H _2L〜1，1），HO-2-O_2N-4-C_6H _3-NHNC { C（O）CH_3} _2（H_2L〜2，2），HO-2-C_6H_4-NHNCC（O）CH_2C（CH_3）_2CH_2C（O）（H_2L〜3，3）或HO-2-O _2N-4- C_6H_3-NHNCC（O）CH_2C（CH _3）_2CH_2C（O）（H_2L〜4，4）。它们的特征已得到充分表征，即通过X射线衍射分析揭示了形成1D链（5和6），2D层（7）或3D网络（8）的广泛的H键。确定了溶液中H_2L〜2与Zn（ii）反应的热力学参数以及1-8的热分解参数。配合物5-8充当硝基醛（亨利）反应的非对映选择性催化剂。 β-硝基链烷醇产品的苏/非对映非对映选择性范围为8：1至1:10，典型收率为80-99％，具体取决于所用的催化剂和底物。

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《Dalton transactions: An international journal of inorganic chemistry》 |2011年第19期|共10页
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Kopylovich M.N.; Mac Leod T.C.O.; Mahmudov K.T.; Guedes Da Silva M.F.C.; Pombeiro A.J.L.;
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1. Zinc(ii) ortho-hydroxyphenylhydrazo-β-diketonate complexes and their catalytic ability towards diastereoselective nitroaldol (Henry) reaction [J] . Kopylovich M.N., Mac Leod T.C.O., Mahmudov K.T., Dalton transactions: An international journal of inorganic chemistry . 2011,第19期

机译：邻位羟基苯基肼-β-二酮酸锌（ii）配合物对非对映选择性硝基羟醛（Henry）反应的催化能力
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3. Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction [J] . Bruno G. M. Rocha, Tatiana C. O. Mac Leod, M. Fátima C. Guedes da Silva, Dalton transactions: An international journal of inorganic chemistry . 2014,第40期

机译：Ni〜（II），Cu〜（II）和Zn〜（II）与空间受阻的蝎子配体（Tpms〜（Ph））的配合物以及在非对映选择性硝基醛（Henry）反应中的催化应用
4. Diastereoselective nitroaldol reaction catalyzed by chiral copper-diamine complexes. [C] . Rafal Kowalczyk, Jacek Skarzewski European Symposium on Organic Chemistry . 2009

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6. Asymmetric catalytic Mannich-type reaction of hydrazones with difluoroenoxysilanes using imidazoline-anchored phosphine ligand–zinc(II) complexes [O] . Zhiliang Yuan, Liangyong Mei, Yin Wei, -1

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7. NiII, CuII and ZnII complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective nitroaldol (Henry) reaction [O] . Rocha Bruno G. M., MacLeod Tatiana C. O., Silva M. Fátima C. Guedes da, 2014

机译：NiII，CuII和ZnII与空间受阻的蝎子配体（TpmsPh）的配合物以及在非对映选择性硝基羟醛（Henry）反应中的催化应用

Zinc(ii) ortho-hydroxyphenylhydrazo-β-diketonate complexes and their catalytic ability towards diastereoselective nitroaldol (Henry) reaction

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