唐除痴
手性有机催化方面,有时也涉及手性金属催化及手性辅助剂诱导的不对称合成反应
个性化签名
- 姓名:唐除痴
- 目前身份:
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学术头衔:
博士生导师
- 职称:-
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学科领域:
有机化学
- 研究兴趣:手性有机催化方面,有时也涉及手性金属催化及手性辅助剂诱导的不对称合成反应
不对称催化的发现和应用是30年来有机化学中取得的最具挑战性的成果之一。手性药物工业的迅速崛起是不对称催化快速发展的原动力。专家预测,21世纪无疑将是手性的世纪,今后若干年在有机化学中不对称反应仍将是最活跃的研究领域。2001年诺贝尔化学奖授予W. Knowles(美)、R. Noyori(野依良治)(日)和K. B. Sharpless三位在不对称催化及其工业应用中做出杰出贡献的科学家,从另一方面印证了上述预测的正确。不对称催化包括手性金属催化和手性非金属催化(即有机催化)两方面。前者已有30多年的历史,取得了许多突破性的进展,包括一些工业上的应用,它已成为不对称催化领域的主流研究方向。而手性有机催化虽然有较长的历史,但真正受到关注还是近十几年的事, 现在也已步入了它的黄金时代,成为不对称催化的非主流方向。我们课题组从上世纪90年代中开始不对称合成研究工作,主要精力在手性有机催化方面,有时也涉及手性金属催化及手性辅助剂诱导的不对称合成反应。曾合成过几十种手性三、四配位磷化合物用于多种不对称反应。如潜手性酮和亚胺的硼烷还原反应、醛的烷基化和硅氰化反应、环氧化合物的开环及动力学拆分反应以及不对称Baylis-Hillman反应等,其中有些工作取得了很好的结果。本课题组的特点是有机磷试剂在不对称合成中的应用,特别是将手性有机磷试剂作为有机催化剂用于各种催化不对称反应,今后还将在这方面合成更多的手性磷化合物,并扩大不对称反应的类型,争取有更多、更好的结果问世。本课题组除博士生和硕士生之外,近年来年轻有为的赵国锋教授(博士)和敬业博学的周正洪副教授(博士)的加盟,不但增强了实力,而且可以继往开来、推进发展,是值得庆幸的事。多年来本课题组多次得到国家自然科学基金及教育部多项基金的资助,在此一并表示谢意。
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唐除痴, Zhuohong Yang, Zhenghong Zhou, * Ke He, Lixin Wang, Guofeng Zhao, Qilin Zhou, Chuchi Tang*
Tetrahedron: Asymmetry 14(2003)3937-3941,-0001,():
-1年11月30日
Some new chiral cyclic o-hydroxylarylphosphonodiamides were synthesized from (−)-χ-phenylethylamine and found to be efficient ligands for the Ti (OPr-i)4 catalyzed asymmetric trimethylsilylcyanation of aromatic aldehydes. Corresponding cyanohydrins were obtained in good chemical yield and enantiomeric excesses up to 90%.
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唐除痴, Kangying Li, a Zhenghong Zhou, a Lixin Wang, a Qifa Chen, b Guofeng Zhao, a Qilin Zhoua, Chuchi Tanga, *
Tetrahedron: Asymmetry 14(2003)95-100,-0001,():
-1年11月30日
Two types of chiral phosphinamide catalysts 3a-d and 4a-c were prepared from L-phenylalanine and L-proline, respectively. Their applications in the asymmetric borane reduction of prochiral ketones were investigated. The chiral secondary alcohols were obtained with excellent chemical yields and moderate to high enantiomeric excesses.
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唐除痴, Zhaoming Li, Zhenghong Zhou, Lixin Wang, Qilin Zhou and Chuchi Tang*
Tetrahedron: Asymmetry 13(2002)145-148,-0001,():
-1年11月30日
The enantioselective reaction of racemic secondary alcohols with phthalimide has been carried out in the presence of a chiral cyclic phosphoramidite (+)-1/DEAD under Mitsunobu reaction conditions. Phthalimide reacted preferentially with the (−)-enantiomer of the alcohol to give a substituted imide (+)-2, while the unreacted enantiomeric alcohol, (+)-3 was obtained in enantiomerically enriched form. Compound (+)-2 was further treated with hydrazine hydrate to form the product amine, (+)-4.
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唐除痴, Zhuo-Hong Yang, Li-Xin Wang, Zheng-Hong Zhou, Qi-Lin Zhou and Chu-Chi Tang*
Tetrahedron: Asymmetry 12(2001)1579-1582,-0001,():
-1年11月30日
The new chiral Schiff base ligands 1a-1c were synthesized from (1R)-(+)-camphor and found to be efficient catalysts for the enantioselective silylcyanation of aromatic aldehydes. The corresponding aromatic cyanohydrins were obtained in good yields and with enantiomeric excesses (e.e.s) of up to 73%.
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唐除痴, Ke He, Zhenghong Zhou, * Lixin Wang, Kangying Li, Guofeng Zhao, Qilin Zhou, and Chuchi Tang
Tetrahedron 60(2004)10505-10513,-0001,():
-1年11月30日
Some new chiral bifunctional o-hydroxyarylphosphonodiamides were synthesized starting from (C)-cis-1, 2, 2-trimethylcyclopentane-1, 3-diamine and the absolute configuration of the phosphorus atom was determined by X-ray diffraction analysis. Excellent enantioselectivity (up to 98% ee) was achieved in asymmetric silylcyanation of aromatic aldehydes using a chiral titanium complex formed in situ from Ti (OiPr)4 and o-hydroxyarylphosphonodiamide as the catalyst.
Chiral cyclophosphonodiamide, Asymmetric silylcyanation, Catalysis, Enantioselectivity, Aromatic aldehyde.,
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唐除痴, Zhou Zhenghong, Tang Yilong, Wang Lixin, Zhao Guofeng, Zhou Qilin, Tang Chuchi*
SYNTHESIS 2004, No.2, pp 0217-0220,-0001,():
-1年11月30日
α-Disubstituted pyrrolidine-2-methanols were synthesized starting from L-proline and their application as chiral auxiliary in the asymmetric NaBH4 reduction of α, β-unsaturated triazolyl ketones was investigated. The corresponding α, β-unsaturated triazolyl alcohol derivatives (Uniconazole and Diniconazole) were obtained in good chemical yields with high ee values (up to 93%).
triazoles,, L-proline,, asymmetric reduction
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唐除痴, Ke He, Zhenghong Zhou, * Lixin Wang, Kangying Li, Guofeng Zhao, Qilin Zhou, Chuchi Tang
SYNLETT 2004, No.9, pp 1521-1524,-0001,():
-1年11月30日
A new chiral cyclic o-hydroxynaphthylphosphonodiamide (+)-2 was synthesized starting from (+)-cis-1, 2, 2-trimethylcyclopentane-1, 3-diamine. The absolute configuration of phosphorus atom was determined as S by X-ray diffraction analysis. Excellent enantioselectivity (up to 98.3% ee) was achieved in asymmetric silylcyanation of aromatic aldehydes using a chiral titanium complex prepared in situ from Ti (Oi-Pr)4 and (+)-2 as the catalyst.
chiral phosphonodiamide,, asymmetric silylcyanation,, catalysis,, enantioselectivity,, aromatic aldehyde
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唐除痴, Juexiao Cai, Zhenghong Zhou, Guofeng Zhao, and Chuchi Tang*
ORGANIC LETTERS 2002 Vol. 4, No.26 4723-4725,-0001,():
-1年11月30日
In homogeneous H2O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield. In this reaction, Me3N, DMAP, DABCO, and urotropine were good catalysts. Except for low-carbon alcohols, tetrahydrofuran, 1,4-dioxane, and acetonitrile could be chosen as the solvent. Under this condition, the diastereoselective reaction of nitrobenzaldehyde and L-menthyl acrylate was realized with 88-99% de.
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唐除痴, Li Kangying, Zhou Zhenghong, Zhao Guofeng, Tang Chuchi
Heteroatom Chemistry Volume 14, Number 6, 2003,-0001,():
-1年11月30日
Eleven chiral trivalent or quatrivalent phosphorus reagents were synthesized starting from L-proline, D-camphor, (+)-or(−)-1, 1'-binaphthalene-2, 2'-diol, (−)-α-phenylethylamine, etc. and their application as catalysts in asymmetric borane reduction of N-phenyl imine of acetophenone was preliminarily investigated. N-Phenyl α-phenylethylamine was obtained in good yield with low to moderate enantioselectivity.
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【期刊论文】Convenient Synthesis of Optically Active α-Hydroxyphosphinic Acids
唐除痴, Juexiao Cai, Zhenghong Zhou, Guofeng Zhao, and Chuchi Tang
Heteroatom Chemistry Volume 14, Number 4, 2003,-0001,():
-1年11月30日
The reaction of O-menthyl phenylphosphonite 1 with aromatic aldehydes in the presence of Me3SiCl provided the O-menthyl α-hydroxyphosphinates 2. Acidic hydrolysis of 2 gave the corresponding α-hydroxyphosphinic acids 3. The (+)-enantiomer of 3a and 3b, adduct of benzaldehyde and 4-methylbenzaldehyde respectively, were obtained via multiple recrystallization. The absolute configuration of (+)-3a was determined as S by X-ray crystallography.
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