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通过铑催化的外消旋烯丙基氯的烯丙基芳基化实现高度对映选择性的日向交叉偶联反应。

Highly Enantioselective Hiyama Cross-Coupling via Rh-Catalyzed Allylic Arylation of Racemic Allyl Chlorides.

作者信息

González Jesús, Schäfer Philipp, Fletcher Stephen P

机构信息

Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, United Kingdom.

出版信息

Organometallics. 2019 Oct 28;38(20):3991-3995. doi: 10.1021/acs.organomet.9b00197. Epub 2019 May 10.

DOI:10.1021/acs.organomet.9b00197
PMID:32055086
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7009026/
Abstract

Highly enantioselective Hiyama cross-coupling reactions have been achieved through rhodium(I)-catalyzed dynamic kinetic asymmetric transformations between aryl siloxanes and cyclic racemic allyl halides. This process affords valuable enantiomerically enriched aryl-substituted cyclic allyl products and is compatible with heterocyclic allyl chloride electrophiles.

摘要

通过铑（I）催化芳基硅氧烷与环状外消旋烯丙基卤化物之间的动态动力学不对称转化，实现了高度对映选择性的日山交叉偶联反应。该过程提供了有价值的对映体富集的芳基取代环状烯丙基产物，并且与杂环烯丙基氯亲电试剂兼容。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/dd7450162847/om9b00197_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/79eab82fef3f/om9b00197_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/d48a8dcc6869/om9b00197_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/11bc7e6ec815/om9b00197_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/dd7450162847/om9b00197_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/79eab82fef3f/om9b00197_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/d48a8dcc6869/om9b00197_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/11bc7e6ec815/om9b00197_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a833/7009026/dd7450162847/om9b00197_0004.jpg

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Chem Commun (Camb). 2017 Nov 21;53(93):12499-12511. doi: 10.1039/c7cc07151e.
2
Asymmetric Suzuki-Miyaura coupling of heterocycles via Rhodium-catalysed allylic arylation of racemates.通过铑催化的外消旋烯丙基芳基化反应实现杂环的不对称铃木-宫浦偶联反应。
Nat Commun. 2017 Jun 13;8:15762. doi: 10.1038/ncomms15762.
3
Mechanistic Studies on a Cu-Catalyzed Asymmetric Allylic Alkylation with Cyclic Racemic Starting Materials.
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4
The Hiyama Cross-Coupling Reaction: New Discoveries.桧山交叉偶联反应：新发现
Chem Rec. 2016 Dec;16(6):2521-2533. doi: 10.1002/tcr.201600063. Epub 2016 Jul 14.
5
Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans.铜催化烷基锆烯对消旋3,6-二氢-2H-吡喃的不对称烯丙基烷基化反应。
Beilstein J Org Chem. 2015 Dec 3;11:2435-43. doi: 10.3762/bjoc.11.264. eCollection 2015.
6
Rhodium-catalysed asymmetric allylic arylation of racemic halides with arylboronic acids.铑催化的外消旋卤代物与芳基硼酸的不对称烯丙基芳基化反应。
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7
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8
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9
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10
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Nature. 2015 Jan 15;517(7534):351-5. doi: 10.1038/nature14089.