Stereoselective Preparation and Reactions of Configurationally Defined Dialkylzinc Compounds

Boudier Andreas; Darcel Christophe; Flachsmann Felix; Micouin Laurent; Oestreich Marti

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Stereoselective Preparation and Reactions of Configurationally Defined Dialkylzinc Compounds

机译：立体定义的二烷基锌化合物的立体制备及反应

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The reaction of cyclic and open-chain diastereomerically pure secondary organoboranes wiht diisopropylzinc allows the preparation of secondary dialkylzinc reagents with good to excellent retention of configuration as shown by deuterolysis and Cu~I_and Pd~0-mediated reactions with electrophiles. The importance of a high boron-zinc exchange rate to obtien high diastereoselevtivity has been shown. Improvement of the configurational stability and stereomeric purity of the zinc intermediates has been obtained by using mono-isopinocamphenylborane ((-)-IpcBH_2) providing optically active dialkylzinc compounds (up to 96% ee) with enhanced diastereoselectivities.

机译：环和开链非对映异构纯的仲有机硼烷与二异丙基锌的反应使得可以制备仲二烷基锌试剂，具有良好的构型保留，如氘化以及Cu〜I_和Pd〜0介导的亲电反应所示。已经显示出高的硼-锌交换率对维持高的非对映性的重要性。锌中间体的构型稳定性和立体纯度的改善已通过使用单-异op基苯甲硼烷（（-）-IpcBH_2）获得，其光学活性的二烷基锌化合物（至多96％ee）具有非对映选择性。

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《Chemistry: A European journal》 |2000年第15期|共14页
作者
Boudier Andreas; Darcel Christophe; Flachsmann Felix; Micouin Laurent; Oestreich Marti;
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正文语种 eng
中图分类化学;应用化学;
关键词
boron-zinc exchange organozinc compounds; stereoselective synthesis; zinc;

机译：硼锌交换有机锌化合物立体选择性合成锌;

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1. Stereoselective Preparation and Reactions of Configurationally Defined Dialkylzinc Compounds [J] . Boudier Andreas, Darcel Christophe, Flachsmann Felix, Chemistry: A European journal . 2000,第15期

机译：立体定义的二烷基锌化合物的立体制备及反应
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6. HPLC Separation of Diastereomers: Chiral Molecular Tools Useful for the Preparation of Enantiopure Compounds and Simultaneous Determination of Their Absolute Configurations [O] . Nobuyuki Harada 2016

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7. Alkylation Reactions of Dialkylzinc Compounds with 1,4- Diaza- 1,3-butadienes: Cationic and radical Anionic Organozinc Intermediates. Molecular Structure of the Cationic Organozinc Species MeZn(t-BuN=CHCH=N-t-Bu)O(_3)SCF(_3) and Me(_2)Zn(bpy)(bpy = 2,2' -Bipyridine) [O] . Wissing Elmo, Kaupp Martin, Boersma Jaap, 2012

机译：二烷基锌化合物与1,4-二氮杂1,3,3-丁二烯的烷基化反应：阳离子和自由基阴离子有机锌中间体。阳离子有机锌物种的分子结构MeZn（t-BuN = CHCH = Nt-Bu） O （_ 3 ）SCF （_ 3 ）和Me （_ 2 ）Zn（bpy）（bpy = 2,2 '-联吡啶

Stereoselective Preparation and Reactions of Configurationally Defined Dialkylzinc Compounds

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