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本文引用的文献

1
Catalytic enantioselective one-pot aminoborylation of aldehydes: a strategy for construction of nonracemic α-amino boronates.醛的催化对映选择性一锅法氨基硼化反应：构建非外消旋 α-氨基硼酸酯的策略。
J Am Chem Soc. 2013 Jun 26;135(25):9252-4. doi: 10.1021/ja402569j. Epub 2013 Jun 13.
2
Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their in situ site-, diastereo-, and enantioselective additions to aldehydes and ketones.铜催化的2-(频哪醇硼酸酯)硼取代烯丙基铜配合物的化学选择性制备及其对醛和酮的原位位点、非对映体和对映体选择性加成反应。
Angew Chem Int Ed Engl. 2013 May 3;52(19):5046-51. doi: 10.1002/anie.201301018. Epub 2013 Apr 3.
3
NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism.NHC-Cu 催化的单取代丙二烯的原硼化反应。配体控制的位点选择性、在合成和机理中的应用。
Org Lett. 2013 Mar 15;15(6):1414-7. doi: 10.1021/ol4004178. Epub 2013 Mar 5.
4
Exceptionally E- and β-selective NHC-Cu-catalyzed proto-silyl additions to terminal alkynes and site- and enantioselective proto-boryl additions to the resulting vinylsilanes: synthesis of enantiomerically enriched vicinal and geminal borosilanes.异常的 E- 和 β-选择性 NHC-Cu 催化的末端炔烃的原硅烷基加成以及生成的乙烯基硅烷的位点和对映选择性原硼酸酯加成：对映体富集的偕二硼硅烷和连二硼硅烷的合成。
Chemistry. 2013 Feb 25;19(9):3204-14. doi: 10.1002/chem.201203803. Epub 2013 Jan 16.
5
Chiral copper(II)-catalyzed enantioselective boron conjugate additions to α,β-unsaturated carbonyl compounds in water.手性铜（II）催化的对映选择性硼对水中α，β-不饱和羰基化合物的共轭加成反应。
Angew Chem Int Ed Engl. 2012 Dec 14;51(51):12763-6. doi: 10.1002/anie.201207343. Epub 2012 Nov 19.
6
Regioselective catalytic hydroboration of propargylic species using Cu(I)-NHC complexes.使用 Cu(I)-NHC 配合物对丙炔基物种进行区域选择性催化硼氢化反应。
Org Lett. 2012 Sep 21;14(18):4790-3. doi: 10.1021/ol302086v. Epub 2012 Sep 4.
7
Metal-free catalytic enantioselective C-B bond formation: (pinacolato)boron conjugate additions to α,β-unsaturated ketones, esters, Weinreb amides, and aldehydes promoted by chiral N-heterocyclic carbenes.无金属催化的对映选择性 C-B 键形成：手性 N-杂环卡宾促进的（频哪醇硼酸酯）硼与α,β-不饱和酮、酯、Weinreb 酰胺和醛的加成反应。
J Am Chem Soc. 2012 May 16;134(19):8277-85. doi: 10.1021/ja302929d. Epub 2012 May 4.
8
Regiocontrolled Cu(I)-catalyzed borylation of propargylic-functionalized internal alkynes.区域控制的炔丙基官能化内部炔烃的 Cu(I)催化硼化反应。
J Am Chem Soc. 2012 May 2;134(17):7219-22. doi: 10.1021/ja300627s. Epub 2012 Apr 18.
9
Asymmetric synthesis of α-amino boronate esters via organocatalytic pinacolboryl addition to tosylaldimines.通过有机催化的频哪醇硼烷加成到对甲苯磺酰亚胺实现α-氨基硼酸酯的不对称合成。
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10
Copper-catalyzed highly regio- and stereoselective directed hydroboration of unsymmetrical internal alkynes: controlling regioselectivity by choice of catalytic species.铜催化不对称内炔的高度区域和立体选择性导向硼氢化反应：通过催化物种的选择控制区域选择性
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通过氮杂环卡宾催化（频哪醇硼酸酯）硼单元与烯酮的共轭加成反应对硼取代的季碳立体中心进行对映选择性合成。

Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

作者信息

Radomkit Suttipol, Hoveyda Amir H

机构信息

Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 (USA).

出版信息

Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3387-91. doi: 10.1002/anie.201309982. Epub 2014 Feb 24.

DOI:10.1002/anie.201309982
PMID:24615958
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4094110/
Abstract

The first examples of Lewis base catalyzed enantioselective boryl conjugate additions (BCAs) that generate products containing boron-substituted quaternary carbon stereogenic centers are disclosed. Reactions are performed in the presence of 1.0-5.0 mol% of a readily accessible chiral accessible N-heterocyclic carbene (NHC) and commercially available bis(pinacolato)diboron; cyclic or linear α,β-unsaturated ketones can be used and rigorous exclusion of air or moisture is not necessary. The desired products are obtained in 63-95% yield and 91:9 to >99:1 enantiomeric ratio (e.r.). The special utility of the NHC-catalyzed approach is demonstrated in the context of an enantioselective synthesis of natural product antifungal (-)-crassinervic acid.

摘要

首次公开了路易斯碱催化的对映选择性硼基共轭加成（BCA）的实例，该反应生成含有硼取代季碳立体中心的产物。反应在1.0 - 5.0 mol%易于获得的手性可及氮杂环卡宾（NHC）和市售双（频哪醇）二硼存在下进行；环状或线性α,β-不饱和酮均可使用，无需严格排除空气或水分。所需产物的收率为63 - 95%，对映体比例（e.r.）为91:9至>99:1。在天然产物抗真菌剂（-）-厚叶石蒜碱的对映选择性合成中展示了NHC催化方法的特殊效用。