Absolute asymmetric synthesis by nucleophilic carbonyl addition using chiral crystals of achiral amides

Masami Sakamoto; Shuichiro Kobaru; Takashi Mino; Tsutomu Fujita

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Absolute asymmetric synthesis by nucleophilic carbonyl addition using chiral crystals of achiral amides

机译：使用非手性酰胺的手性晶体通过亲核羰基加成进行绝对不对称合成

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摘要

Reaction of the chiral crystals of the achiral amides with n-butyllithium in toluene at -80 ℃ gave optically active alcohols in 17-84% ee.

机译：在-80℃下，非手性酰胺的手性晶体与正丁基锂在甲苯中的反应得到旋光性醇，其含量为17-84％ee。

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《Chemical Communications》 |2004年第8期|p.1002-1003|共2页
作者
Masami Sakamoto; Shuichiro Kobaru; Takashi Mino; Tsutomu Fujita;
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Department of Materials Technology, Faculty of Engineering, Chiba University, Yayoi-cho, Chiba 263-8522, Japan;

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正文语种 eng
中图分类化学;
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入库时间 2022-08-17 13:33:11

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2. Spontaneous chiral crystallization of achiral materials and absolute asymmetric photochemical transformation using the chiral crystalline environment [J] . Sakamoto M Journal of photochemistry and photobiology, C. Photochemistry reviews . 2006,第4期

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3. 'Absolute' Asymmetric Synthesis Using the Chiral Crystal Environment: Photochemical Hydrogen Abstraction from Achiral Acyclic Monothioimides in the Solid State [J] . Masami Sakamoto, Masaki Takahashi, Motoki Shimizu, The Journal of Organic Chemistry . 1995,第22期

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4. Amide-Selective Nucleophilic Addition:Application to Synthesis ofTetrahydroisoquinoline Frameworks and Back-Bone Modificationof Peptides [C] . Yoshito Takahashi, Tastuya Mori, Risa Yoshii 日本化学会春季年会 . 2020

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5. Synthesis of novel chiral phosphinite, phosphite and phosphinous amide ligands and their applications on the asymmetric catalytic reactions. [D] . Guo, Rongwei. 2002

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6. Generation of Absolute Controlled Crystal Chirality by the Removal of Crystal Water from Achiral Crystal of Nucleobase Cytosine [O] . Tsuneomi Kawasaki, Yuko Hakoda, Hiroko Mineki, -1

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7. Determination of the absolute structure of the chiral crystal consisting of achiral dibutylhydroxytoluene and asymmetric autocatalysis triggered by this chiral crystal [O] . Matsumoto Arimasa, Takeda Sora, Harada Shunya, 2016

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8. Nucleophilic Addition of Phosphines to Carbonyl Groups. Isolation of 1-HydroxyPhosphonium and 1-(Trimethylsiloxy) Phosphonium Salts and the Crystal Structure of (1-Hydroxy-1-methylethyl)triethylphosphonium Bromide [R] . Lee, S. W., Trogler, W. C. 1990

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Absolute asymmetric synthesis by nucleophilic carbonyl addition using chiral crystals of achiral amides

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