许家喜
(1) 不对称催化合成,包括设计合成新型手性配体和手性催化剂,开发新的不对称催化反应; (2) 手性药物合成; 手性天然和非天然化合物合成;(3) 生物活性的氨基酸和肽类化合物的合成。
个性化签名
- 姓名:许家喜
- 目前身份:
- 担任导师情况:
- 学位:
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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:(1) 不对称催化合成,包括设计合成新型手性配体和手性催化剂,开发新的不对称催化反应; (2) 手性药物合成; 手性天然和非天然化合物合成;(3) 生物活性的氨基酸和肽类化合物的合成。
1963年出生,博士,教授。1987年毕业于北京大学化学系,获理学士,1992年于北京大学化学系获理学博士学位。1992-1994在北京医科大学(现北京大学医学部)药学院做博士后研究。1994年任北京大学化学与分子工程学院副教授。1995,8-1996,2香港中文大学化学系访问副研究员, 2000-2002年美国科罗拉多州立大学化学系和Vanderbilt大学医学院微生物和免疫学系博士后,2004年任北京大学化学与分子工程学院教授。另外,他还兼任《Molecules》杂志中国地区编委。主要从事的研究领域为:(1) 不对称催化合成,包括设计合成新型手性配体和手性催化剂,开发新的不对称催化反应; (2) 手性药物合成; 手性天然和非天然化合物合成;(3) 生物活性的氨基酸和肽类化合物的合成。迄今己发表研究论文160余篇,其中SCI收录论文100余篇,EI收率论文20余篇,参编著作2部,合译著作1部。论文已被他人引用150余次。承担和完成的主要科研项目有:国家自然科学基金4项、教育部优秀青年教师资助计划项目1项。
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主页访问
2295
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0
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成果阅读
421
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成果数
10
许家喜, Yong Liang, Lei Jiao, Shiwei Zhang, and Jiaxi Xu
J. Org. Chem, Vol. 70, No.1, 2005 337,-0001,():
-1年11月30日
Reactions of ketenes generated from R-diazoketones with a series of acyclic and cyclic imines were investigated under both microwave and photoirradiation conditions. The results indicate that the zwitterionic azabutadiene-type intermediates yielded from imines and ketenes undergo a conrotatory ring closure exclusively to produce-lactams. It is notable that no Woodward-Hoffmann product was found under the ultraviolet irradiation. The photoirradiation-induced Staudinger reaction shows a different stereoselectivity from the electrocyclic reaction of substituted 1,3-butadiene.
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许家喜, Jiaxi Xu, Tiezheng Wei, and Qihan Zhang
J. Org. Chem., Vol. 69, No.20, 2004,-0001,():
-1年11月30日
The influence of electronic effects on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been observed and investigated with use of parasubstituted acetophenones and propiophenones with a variety of functional groups and Bunsubstituted and B-methoxyoxazaborolidines derived from (S)-2-(diphenylhydroxymethyl)-pyrrolidine with borane and trimethyl borate as catalysts in toluene and THF. The results indicate that Hammett linear free energy electronic effects on the enantioselectivity in the asymmetric reduction were observed and rationalized. Tuning electronic effects of the catalyst can improve the enantioselectivity in the reduction. Another interesting finding to be noted is that anions heavily affect the enantioselectivity, especially for the B-methoxy catalyst, because of their coordination with the boron atom in the catalysts.
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许家喜, Jiaxi Xu, Linge Ma and Peng Jiao
Chem. Commun., 2004, 1616-1617,-0001,():
-1年11月30日
Highly enantioselective aziridination of chalcones catalyzed by a novel backbone 1,8-bisoxazolidiny lanthracene (AnBOX) and CuOTf with up to>9% ee and the opposite enantioselectivity compared with the ligands of Evans are described.
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【期刊论文】A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines
许家喜, Jiaxi Xu, Shu Xu
Synthesis 2004, No.2, 276-282,-0001,():
-1年11月30日
N-Benzyloxycarbonyl protected substituted and, disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of substituted and, disubstituted sulfonopeptides.
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许家喜, Jiaxi Xu, Tiezheng Wei, and Qihan Zhang
J. Org. Chem, Vol. 68, No.26, 2003 10151,-0001,():
-1年11月30日
The effect of temperature on the enantioselectivity of the oxazaborolidine-catalyzed asymmetric borane reduction of ketones has been investigated carefully using alkyl aryl ketones with a variety of functional groups and a B-methoxyoxazaborolidine derived from trimethyl borate and (S)- R,Rdiphenylprolinol as a catalyst. The reductions were carried out over a range of temperatures in THF and toluene with or without the catalyst. The reductive rates increase along with increasing reaction temperature with or without the catalyst by determining the conversion of the ketones to alcohols by GC analysis. However, the rates of the catalytic reductions increase faster than those without the catalyst. The results indicate that the noncatalytic borane reduction is an important factor to the enantioselectivity in the reduction. The highest enantioselectivities were usually obtained between 20 and 30℃ in the asymmetric reduction.
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许家喜, Jiaxi Xu, Xianbin Su and Qihan Zhang
Asymmetry 14 (2003) 1781-1786,-0001,():
-1年11月30日
and practical preparation of homochiral linear secondary alcohols, 1-(4-alkylphenyl) and 1-(4- alkoxylphenyl) alcohols, via the asymmetric oxazaborolidine-catalyzed borane reduction of prochiral ketones is described. The phenomenon of the enantioselectivity of 1-(4-alkoxylphenyl) alcohols lower than that of 1-(4-alkylphenyl) alcohols was found and rationalized to the coordination of the oxygen atom in the alkoxy groups to the catalyst and borane. Based on the rationale, the enantioselectivity of 1-(4-alkoxylphenyl) alcohols in the asymmetric reduction was improved with increasing the amount of the catalyst.
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许家喜, Jiaxi Xu
Asymmetry 13 (2002) 1129-1134,-0001,():
-1年11月30日
Abstract-The mechanism for the transformation of β-amino alcohol methanesulfonate hydrochlorides into sodium β-amino alkanesulfonates using sodium sulfite was investigated. The results show that sodium sulfite initially neutralizes the β-amino alcohol methanesulfonate hydrochloride to give a free β-amino alcohol methanesulfonate, which then cyclizes to a 2-alkylaziridine. Attack by the previously formed sodium bisulfite at the less hindered carbon atom of the aziridine ring then yields a β-amino alkanesulfate sodium salt. Based on this mechanistic proposal, a new and rapid asymmetric synthesis of (R)-and (S)-2 β-aminoalkanesulfonic cids from chiral amino alcohols was developed. Chiral amino alcohols were converted to chiral aziridines through the Wenker method or Mitsunobu reaction and the resulting aziridines were reacted with sodium bisulfite to produce chiral β-amino alkanesulfonic acids.
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许家喜, Peng Jiao, a, Jiaxi Xu, Qihan Zhang, Michael C. K. Choib and Albert S. C. Chanb
Asymmetry 12 (2001) 3081-3088,-0001,():
-1年11月30日
Five pairs of novel C2-symmetric and enantiomerically pure bisbenzoxazoles and a pair of bisbenzothiazoles derived from L-and D-tartaric acids have been synthesized from L-and D-2, 3-O-isopropylidenetartaric dichlorides and o-aminophenol derivatives or o-aminothiophenol, respectively, in two-or one-step reactions. The mechanism for the formation of bisbenzoxazoles and bisbenzothiazoles was suggested. The UV and 1H NMR spectra showed that no coordination between the bisbenzoheterazoles and Cu (Ⅰ) or Ni (Ⅱ) cations occurred due to the lack of a sufficiently basic nitrogen donor atom in the benzoheterazole moiety.
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【期刊论文】Chemoselectivity in reactions of an a-diazo-diketone with some conjugative double-bond systems
许家喜, Jiaxi Xu, Qihan Zhang, Liangbi Chen and Hui Chen
Chem. Soc., Perkin Trans. 1, 2001, 2266-2268,-0001,():
-1年11月30日
Reactions of 2-diazo-1,3-diphenylpropane-1,3-dione with α, β-unsaturated aldehydes and ketones, and keto-imines, in refluxing anhydrous toluene indicate that benzoyl (phenyl) ketene, which is generated by the thermal Woldffrearrangement of 2-diazo-1, 3-diphenylpropane-1, 3-dione, shows a pronounced tendency to form chemospecific [2+4] Diels-Alder adducts with the carbonyl group in α, β-unsaturated aldehydes and ketones, and the imine group in keto-imines. The reactivity in reactions of the α-diazo-β-diketone with these conjugative double-bond systems is C=N>C=O>C=C. However, benzoyl (phenyl) ketene reacts with α, β-unsaturated imines to produce chemospecific [2=2] cycloadducts: β-lactams.
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许家喜, Jiaxi Xu and Nanyan Fu
Chem. Soc., Perkin Trans. 1, 2001, 1223-1226,-0001,():
-1年11月30日
Unsymmetrical N-benzyloxycarbonyl-protected 1-amino-1-arylalkylphosphonate mixed diesters were synthesized using a one-pot reaction involving benzyl carbamate, aromatic aldehydes and alkoxydichlorophosphine, followed by treatment with alcohols in the presence of triethylamine. The reactions were followed by 31P NMR and a mechanism is proposed.
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