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苯并环丁醇和环丁醇的催化对映选择性合成——一种连续还原/C-H官能团化反应。

Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanols a sequential reduction/C-H functionalization.

作者信息

Chen Jun, Shi Zhan, Li Chunyu, Lu Ping

机构信息

Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University 220 Handan Lu Shanghai 200433 P. R. China

出版信息

Chem Sci. 2021 Jul 5;12(31):10598-10604. doi: 10.1039/d1sc02119b. eCollection 2021 Aug 11.

DOI:10.1039/d1sc02119b
PMID:34447553
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8356817/
Abstract

We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.

摘要

我们在此报告一种顺序对映选择性还原/C-H官能化反应，用于构建苯并环丁醇和环丁醇的相邻手性碳中心。该策略的特点是酮的实用对映选择性还原和非对映选择性铱催化的C-H硅基化反应。还探索了进一步的转化反应，包括可控的区域选择性开环反应。此外，该策略已用于三种天然产物叶毒菌素（推测结构）、大根香叶烯醇和香木兰醇的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f72f/8356817/0b274e0b2aee/d1sc02119b-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f72f/8356817/b441b0a12e8b/d1sc02119b-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f72f/8356817/9eeb49f1eb69/d1sc02119b-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f72f/8356817/0f1b1d7266ae/d1sc02119b-s6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f72f/8356817/b441b0a12e8b/d1sc02119b-s1.jpg
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2
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Angew Chem Int Ed Engl. 2020 Dec 1;59(49):21890-21894. doi: 10.1002/anie.202008465. Epub 2020 Sep 23.
3
Transition Metal-Catalyzed Enantioselective C-H Functionalization via Chiral Transient Directing Group Strategies.
J Chem Ecol. 2025 Feb 4;51(1):22. doi: 10.1007/s10886-025-01574-6.
4
Enhanced thermal and photo-stability of a -substituted dicumyl ketone intercalated in a layered double hydroxide.插层于层状双氢氧化物中的α-取代二苯甲酮的热稳定性和光稳定性增强。
Front Chem. 2022 Oct 10;10:1004586. doi: 10.3389/fchem.2022.1004586. eCollection 2022.
5
Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp)-H Functionalization.钯催化通过C(sp)-H官能团化反应合成苯并环丁烯酮衍生的酮硝酮
Org Lett. 2022 Jun 10;24(22):3960-3964. doi: 10.1021/acs.orglett.2c01317. Epub 2022 May 25.
过渡金属催化的手性瞬态导向基团策略的对映选择性 C-H 官能化。
Angew Chem Int Ed Engl. 2020 Nov 2;59(45):19773-19786. doi: 10.1002/anie.202008437. Epub 2020 Aug 25.
4
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5
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6
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8
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9
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Enantioselective C-H Activation with Earth-Abundant 3d Transition Metals.手性 3d 过渡金属 C-H 键活化
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