Pengfei Zhang

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Organization: Hangzhou Normal University

Department: College of Material, Chemistry and Chemical Engineering

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Chemicals
References

A Novel Trypsin-Catalyzed Three-Component Mannich Reaction

Co-reporter:She-Jie Chai;Yi-Feng Lai;Hui Zheng ;Peng-Fei Zhang

Helvetica Chimica Acta 2010 Volume 93( Issue 11) pp:2231-2236

Publication Date(Web):

DOI:10.1002/hlca.201000063

Abstract

We found that the trypsin from hog pancreas displayed high activity to promote three-component Mannich reaction of aromatic aldehydes, aromatic amines, and acetone with moderate-to-excellent yields. The reaction tolerates a great range of substrates and extends the application of trypsin in organic synthesis.

A Novel 1-Glycosyl-1H-triazole-Based P,N Ligand for Rhodium-Catalyzed Asymmetric Hydrosilylation of Ketones

Co-reporter:Chao Shen;Peng-Fei Zhang;Xin-Zhi Chen

Helvetica Chimica Acta 2010 Volume 93( Issue 12) pp:2433-2438

Publication Date(Web):

DOI:10.1002/hlca.201000093

Abstract

A novel class of chiral glycosyl-triazole-based P,N ligands were synthesized by ‘click chemistry’ and were applied to the Rh-catalyzed asymmetric hydrosilylation of a range of substituted acetophenones. Enantioselective hydrosilylation of acetophenone gave (S)-1-phenylethanol in moderate enantioselectivity (72% ee) and in good conversion (93%).

Diastereoselective alkynylation of glucose-modified imines with terminal alkynes

Co-reporter:Jiangang Mao, Pengfei Zhang

Tetrahedron: Asymmetry 2009 Volume 20(Issue 5) pp:566-569

Publication Date(Web):25 March 2009

DOI:10.1016/j.tetasy.2009.02.056

The copper(I)-catalyzed enantioselective alkynylation of aldimines incorporating a 2,3,4,6-tetrakis-O-pivaloyl-d-glucopyranosyl (Piv4Glc) chiral auxiliary with terminal alkynes is reported. The present system provides a versatile tool for the construction of optically active propargylamine derivatives. Good yields and enantiomeric excess values were achieved with an array of imines and biologically active, propargylamine derivatives.N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1,3-diphenylprop-2-ynylamineC41H55NO9De = 90%[α]D20=+30.55 (c 0.036, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-nitrophenyl)-3-phenylprop-2-ynylamineC41H54N2O11De = 91%[α]D20=+32.4 (c 0.032, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-chlorophenyl)-3-phenylprop-2-ynylamineC41H54ClNO9De = 93%[α]D20=+36.6 (c 0.023, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(3-trifluoromethyl)penyl-3-phenylprop-2-ynylamineC41H54N2O11De = 96%[α]D20=+16.9 (c 0.043, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-trifluoromethyl)penyl-3-phenylprop-2-ynylamineC42H54F3NO9De = 93%[α]D20=+31.45 (c 0.027, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-methylphenyl)-3-phenylprop-2-ynylamineC42H57NO9De = 92%[α]D20=+17.2 (c 0.073, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4- chlorophenyl)-hept-2-ynylamineC39H58ClNO9De = 78%[α]D20=+11.9 (c 0.056, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)N-(2,3,4,6-Tetra-O-pivaloyl-β-d-glucopyranosyl)-1-(4-chlorophenyl)-3-(trimethylsilyl)-prop-2-ynylamineC38H58ClNO9SiDe = 28%[α]D20=+9.4 (c 0.039, CHCl3)Source of chirality: 2,3,4,6-tetra-O-pivaloyl-β-d-glucopyranoseAbsolute configuration: (R)