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通过与炔丙基碳酸酯的联合交叉偶联实现β-烯丙基硼酸酯的催化对映选择性合成。

Catalytic Enantioselective Synthesis of β-Allenyl Boronic Esters by Conjunctive Cross-Coupling with Propargylic Carbonates.

作者信息

Aparece Mark D, Hu Weipeng, Morken James P

机构信息

Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.

出版信息

ACS Catal. 2019 Dec 6;9(12):11381-11385. doi: 10.1021/acscatal.9b04453. Epub 2019 Oct 31.

DOI:10.1021/acscatal.9b04453
PMID:33692912
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7943035/
Abstract

Enantioselective conjunctive cross-coupling with propargylic carbonates affords (β-boryl allenes as the reaction product. The reaction is found to proceed through the intermediacy of dimethoxyboronate complexes that are generated in situ by a strain-induced ligand exchange reaction.

摘要

与碳酸炔丙酯的对映选择性联合交叉偶联反应生成(β-硼基丙二烯作为反应产物。发现该反应通过应变诱导的配体交换反应原位生成的二甲氧基硼酸酯配合物中间体进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/60a494cfa117/nihms-1564362-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/32f2251c71d1/nihms-1564362-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/1905a95a5800/nihms-1564362-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/b8a9113717d6/nihms-1564362-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/60a494cfa117/nihms-1564362-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/32f2251c71d1/nihms-1564362-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/1905a95a5800/nihms-1564362-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/b8a9113717d6/nihms-1564362-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/766a/7943035/60a494cfa117/nihms-1564362-f0005.jpg

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Angew Chem Int Ed Engl. 2019 Jan 8;58(2):592-595. doi: 10.1002/anie.201811782. Epub 2018 Dec 12.
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Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.硼配体设计实现的非对映选择性和对映选择性共轭交叉偶联。
J Am Chem Soc. 2018 Nov 14;140(45):15181-15185. doi: 10.1021/jacs.8b09909. Epub 2018 Nov 6.
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Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters.串联烯丙基化/1,2-硼酸酯重排用于相邻季碳立体中心吲哚啉的不对称合成
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Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.通过串联交叉偶联对映选择性构建三级硼酸酯。
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Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope.碳水化合物/DBU 共催化烯烃双硼化：机理研究提供了更高的催化效率和底物范围。
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Ni-Catalyzed Enantioselective Conjunctive Coupling with C(sp) Electrophiles: A Radical-Ionic Mechanistic Dichotomy.镍催化的 C(sp) 亲电试剂对映选择性偶联反应：自由基-离子机理二分法。
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Enantiospecific sp -sp Coupling of ortho- and para-Phenols with Secondary and Tertiary Boronic Esters.邻位和对位酚与仲硼酸酯和叔硼酸酯的对映选择性 sp-sp 偶联。
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