B-ISO-2-(2-DIETHYLAMINOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT CHAIN ALIPHATIC KETONES

Weissman SA.; Ramachandran PV.

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B-ISO-2-(2-DIETHYLAMINOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT CHAIN ALIPHATIC KETONES

机译：B-ISO-2-（2-二乙基氨基乙基）APOPINOCAMPHEYL-9-BORABICYCLO [3.3.1]壬基氢化物-改进的直链脂肪族手性还原剂

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A series of chirally modified borohydrides of the type lithium B-iso-2-(alkyl)apopinocampheyl-9-borabicyclo[3.3.1]nonyl hydride (2-4 and 8-9) were prepared to enable a strategic development of chiral reagents for the reduction of straight chain aliphatic ketones. Reagent 8 (alkyl = 2-diethylaminoethyl) reduces 2-octanone in 82% ee, significantly higher than that obtained with NB-Enantride (7) under identical conditions. An improved methodology for these reductions is also described. Copyright (C) 1996 Elsevier Science Ltd [References: 16]

机译：制备了一系列手性修饰的B-异-2-锂（烷基）-apapinocampheyl-9-borabicyclo [3.3.1]壬基氢化锂类型的硼氢化物（2-4和8-9），以实现手性试剂的战略开发用于还原直链脂肪族酮。试剂8（烷基= 2-二乙基氨基乙基）在82％ee中还原2-辛酮，明显高于在相同条件下用NB-Enantride（7）获得的2-辛酮。还描述了用于这些减少的改进方法。版权所有（C）1996 Elsevier Science Ltd [引用：16]

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry》 |1996年第22期|共4页
作者
Weissman SA.; Ramachandran PV.;
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正文语种 eng
中图分类有机化学;
关键词
Asymmetric reduction; Selective reductions; Steric requirements; Prochiral ketones; Reagents; 2-position; Apopinene;

机译：不对称还原;选择性还原;空间需求;手性酮;试剂;2-位;Apopinene;

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1. B-ISO-2-(2-DIETHYLAMINOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT CHAIN ALIPHATIC KETONES [J] . Weissman SA., Ramachandran PV. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 1996,第22期

机译：B-ISO-2-（2-二乙基氨基乙基）APOPINOCAMPHEYL-9-BORABICYCLO [3.3.1]壬基氢化物-改进的直链脂肪族手性还原剂
2. Recyclable chiral diamine-polyoxometalate (POM) acids catalyzed asymmetric direct aldol reaction of aromatic aldehydes with long-chain aliphatic ketones [J] . Qiang Gao, Sheng-Mei Lu, Yan Liu Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2011,第29期

机译：可回收的手性二胺-多金属氧酸盐（POM）催化芳香醛与长链脂肪族酮的不对称直接羟醛反应
3. Origin of the pi-facial stereoselectivity in the addition of nucleophilic reagents to chiral aliphatic ketones as evidenced by high-level ab initio molecular-orbital calculations [J] . Takahashi O, Yamasaki K, Kohno Y, Chemistry, an Asian journal . 2006,第6期

机译：高亲密性从头算分子轨道计算证明，亲核试剂与手性脂肪族酮加成时，面部立体选择性的起源
4. EnantioselectiveReduction of Prochiral Ketones Using NaBH4/Me3SiCl(BF3·OEt2)Reducing Agents and Heterogeneous Chiral Sulfonyamide Catalyst [C] . Jian-bing Hu International symposium for Chinese organic chemists . 2000

机译：使用NaBH4 / ME3SICL（BF3·OET2）降低剂和异质手性硫胺催化剂对促胰酮的映对诱导
5. ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH A CHIRAL REDUCING AGENT PREPARED FROM STANNOUS CHLORIDE, CHIRAL DIAMINE AS A LIGAND, AND DIISOBUTYLALUMINUM HYDRIDE [O] . Takeshi Oriyama, Teruaki Mukaiyama 1984

机译：具有由氯化锡，手性胺作为配体制备的手性还原剂的前三丙酮的不对称还原，以及二异丁基铝氢化物
6. Lithium-B-Iso-2-ethylapopinocampheyl-9-borabicyclo(3.3.1)nonyl Hydride as anImproved Reagent for Asymmetric Reduction of Unhindered Aliphatic Ketones. Further Evidence for the Improved Enantioselectivity in Reductions by Reagents Containing Increased Ster [R] . Ramachandran, P. V., Brown, H. C., Swaminathan, S., 1990

机译：锂-B-Iso-2-乙基哌啶基-9-硼双环（3.3.1）壬基氢化物作为改进的试剂，用于不受阻碍的脂族酮的不对称还原。含有增加的ster的试剂减少对映选择性的进一步证据

B-ISO-2-(2-DIETHYLAMINOETHYL)APOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE - AN IMPROVED CHIRAL REDUCING AGENT FOR STRAIGHT CHAIN ALIPHATIC KETONES

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