Xiao-Fei Huang
Soochow University (Suzhou)
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Publication
Featured researches published by Xiao-Fei Huang.
Organic and Biomolecular Chemistry | 2012
Xiao-Fei Huang; Zhao-Min Liu; Zhi-Cong Geng; Shao-Yun Zhang; Yong Wang; Xing-Wang Wang
Optically active spirocyclohexaneoxindole motifs are very important building blocks for preparations of biologically active complexes, natural products, and pharmaceutical compounds. Herein, we report the syntheses of enantiopure spirocyclohexaneoxindoles through domino Michael-Aldol reactions between isatin derived alkenes and pentane-1,5-dial in the presence of diphenylprolinol silyl ether as an aminocatalyst. As a result, a series of multistereogenic and functionalized spirocyclohexaneoxindoles have been obtained in good yields with moderate diastereoselectivities and excellent enantioselectivities. In addition, electronic circular dichroism (ECD) spectroscopy and time-dependent density functional theory (TD-DFT) were used to investigate the rational structures of spirocyclohexaneoxindoles.
Organic and Biomolecular Chemistry | 2014
Xiao-Fei Huang; Ya-Fei Zhang; Zheng-Hang Qi; Nai-Kai Li; Zhi-Cong Geng; Kun Li; Xing-Wang Wang
A diastereo- and enantio-selective domino Michael-cyclization-tautomerization reaction of isatylidene malononitriles with α,α-dicyanoalkenes catalyzed by a cinchona alkaloid-derived bifunctional thiourea catalyst has been developed. A series of multi-functionalized spiro oxindole diene derivatives have been obtained in good to excellent yields (up to 97%) with good to excellent enantioselectivities (up to 96%) as well as good diastereoselectivities (up to 7.9 : 1). In addition, an anomalous temperature effect on the enantioselectivity has also been studied for this transformation.
Chemical Communications | 2012
Zhi-Cong Geng; Ning Li; Jian Chen; Xiao-Fei Huang; Bin Wu; Guo-Gui Liu; Xing-Wang Wang
Non-naturally enantioenriched cis-β-thio-α-amino acid derivatives were synthesized through one pot, cascade thio-Michael/ring opening reaction of aromatic thiols with (Z)-olefinic azlactones in good yields with high levels of diastereoselectivities and enantioselectivities, which was catalyzed by a chiral bifunctional thiourea-tertiary amine catalyst.
Journal of Organic Chemistry | 2013
Jian Chen; Zhi-Cong Geng; Ning Li; Xiao-Fei Huang; Feng-Feng Pan; Xing-Wang Wang
Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1-ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.
Beilstein Journal of Organic Chemistry | 2012
Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Summary The catalytic synthesis of nitrogen-containing heterocycles is of great importance to medicinal and synthetic chemists, and also a challenge for modern chemical methodology. In this paper, we report the synthesis of pyrazolidine derivatives through a domino aza-Michael/hemiacetal sequence with chiral or achiral secondary amines as organocatalysts. Thus, a series of achiral pyrazolidine derivatives were obtained with good yields (up to 90%) and high diastereoselectivities (>20:1) with pyrrolidine as an organocatalyst, and enantioenriched pyrazolidines are also achieved with good results (up to 86% yield, >10/1 regioselectivity, >20:1 dr, 99% ee) in the presence of (S)-diphenylprolinol trimethylsilyl ether catalyst.
Advanced Synthesis & Catalysis | 2013
Jin-Xin Zhang; Nai-Kai Li; Zhao-Min Liu; Xiao-Fei Huang; Zhi-Cong Geng; Xing-Wang Wang
Tetrahedron | 2014
Zhao-Min Liu; Nai-Kai Li; Xiao-Fei Huang; Bing Wu; Ning Li; Chun-Yuen Kwok; Yong Wang; Xing-Wang Wang
Tetrahedron | 2012
Guo-Gui Liu; Hua Zhao; Yu-Bao Lan; Bin Wu; Xiao-Fei Huang; Jian Chen; Jing-Chao Tao; Xing-Wang Wang
European Journal of Organic Chemistry | 2011
Mei-Qiu Li; Jin-Xin Zhang; Xiao-Fei Huang; Bin Wu; Zhao-Min Liu; Jian Chen; Xiang‐Dong Li; Xing-Wang Wang
European Journal of Organic Chemistry | 2013
Zhi-Cong Geng; Xiang Chen; Jin-Xin Zhang; Ning Li; Jian Chen; Xiao-Fei Huang; Shao-Yun Zhang; Jing-Chao Tao; Xing-Wang Wang