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Quantum chemical study on asymmetric allylation of benzaldehyde in the presence of chiral allylboronate

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2005年第6期6卷 606-610页

作者：陈万锁陈志荣 Center of Unilab Chemical Engineering Reaction & Department of Chemical Engineering Zhejiang University Hangzhou 310027 China

The quantum chemical method is employed to study the modified asymmetric allylation of benzaldehyde controlled by diisopropyl D-(-)-tartrate auxiliary. All the structures are optimized completely at the B3LYP/6-31G(d,p) level. The (R)-secondary alcohol can be achieved mainly through a six-membered ring chair-like transition state structure. From the relative reaction rates theory the main product configuration predicted is in agreement with the experiment result.

关键词： Benzaldehyde asymmetric allylation DFT

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A new convenient asymmetric approach to herbarumin Ⅲ

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Chinese Chemical Letters 2007年第3期18卷 255-257页

作者： Xue Song Chen Shi Jun Da Li Hong Yang Bo Yan Xu Ztfi Xiang Xie Ying Li The State Key Laboratory of Applied Organic Chemistry Institute of Organic Chemistry Lanzhou University Lanzhou 730000 China

The asymmetric total synthesis of herbarumin Ⅲ 3, a naturally occurred phytotoxin, along with 8-epi-herbantmin Ⅲ 22, was succeeded in 12 steps from n-butyraldehyde based on Brown＇s asymmetric allylation, taking mod... 详细信息

关键词： Herbarumin Ⅲ asymmetric allylation Modified Julia olefination Yamaguchi's macro-lactonization

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asymmetric Allyltributylstannane Addition to Ketones Catalyzed by Chiral Indium（Ⅲ）-PYBOX Complex

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Chinese Journal of Chemistry 2006年第10期24卷 1439-1442页

作者：陆军纪顺俊 Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry and Chemical Engineering of Suzhou University Suzhou Jiangsu 215123 China

An indium complex of chiral pyridine bis（oxazoline）（PYBOX） has been applied to the catalytic asymmetric allylation of ketones. It has been found that this chiral indium complex is strong enough to promote the reaction of ketones with allyltributylstannane smoothly. The products were obtained in moderate yields with low to moderate enantioselectivities.

关键词： indium PYBOX asymmetric allylation allyltributylstannane ketone

Preparation of (R)-and (S)-2-Allyl-1,3,2-Dinaphtho(α,β)[d.f]dioxaborepin and Their Reactions with Aldehydes

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Wuhan University Journal of Natural Sciences 2003年第4A期8卷 1138-1142页

作者： Liu De-jun, Shan Zi-xing , Wang Guo-ping, Qin Jin-gui College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, Hubei, China College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 Hubei China

(R)- and (S)-2-Allyl-1,3,2-dinaphtho(α,β)\dioxaborepin ((R)-2 and (S)-2) have been first prepared by the reaction of (R)-(+)- or (S)-(-)-1,1′-bi-2-naphthol and triallylborane in THF at room temperature, respectively. (S)-2 and (R)-2 are sensitive to moisture and oxygen in air and disproportionate easily to triallylborane and 1,1′-bi-2-naphthyl bis(1,1′-bi-2-naphtholborate) at ambient temperature. However, THF is a stabilizer for them. The reactions of (R)-2 or (S)-2 and some aliphetic or aromatic aldehydes in CH_ 2 Cl_ 2 at -78℃ for several hours afforded β-alkylenyl alcohols in up to 84.8% ee. Among them, optically active 1\|(3,5-dichlorophenyl)-3-butenol and 1-(2-methoxyphenyl)-3-butenol were first prepared

关键词： 1,1'-bi-2-naphthyl allylboronate preparation asymmetric allylation

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