Literature DB >> 31538386

Asymmetric Synthesis of 1,4-Dicarbonyl Compounds from Aldehydes by Hydrogen Atom Transfer Photocatalysis and Chiral Lewis Acid Catalysis.

Yulong Kuang1, Kai Wang1, Xiangcheng Shi1, Xiaoqiang Huang2, Eric Meggers2, Jie Wu1,3.   

Abstract

Enantioenriched 1,4-dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for the efficient enantioselective synthesis of these compounds directly from aldehydes through synergistic cooperation between a neutral eosin Y hydrogen atom transfer photocatalyst and a chiral rhodium Lewis acid catalyst. This method is distinguished by its operational simplicity, abundant feedstocks, atom economy, and ability to generate products in high yields (up to 99 %) and high enantioselectivity (up to 99 % ee).
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric synthesis; eosin Y; hydrogen atom transfer; radical umpolung; rhodium

Year:  2019        PMID: 31538386     DOI: 10.1002/anie.201910414

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  10 in total

Review 1.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

Review 2.  Catalytic enantioselective C(sp3)-H functionalization involving radical intermediates.

Authors:  Chi Zhang; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2021-01-20       Impact factor: 14.919

3.  Divergent functionalization of aldehydes photocatalyzed by neutral eosin Y with sulfone reagents.

Authors:  Jianming Yan; Haidi Tang; Eugene Jun Rong Kuek; Xiangcheng Shi; Chenguang Liu; Muliang Zhang; Jared L Piper; Shengquan Duan; Jie Wu
Journal:  Nat Commun       Date:  2021-12-10       Impact factor: 14.919

4.  Syntheses of new chiral chimeric photo-organocatalysts.

Authors:  Jiyaun Lyu; Matteo Leone; Aurélie Claraz; Clémence Allain; Luc Neuville; Géraldine Masson
Journal:  RSC Adv       Date:  2021-11-15       Impact factor: 4.036

5.  Photomediated reductive coupling of nitroarenes with aldehydes for amide synthesis.

Authors:  Qingyao Li; Peng Dai; Haidi Tang; Muliang Zhang; Jie Wu
Journal:  Chem Sci       Date:  2022-08-03       Impact factor: 9.969

6.  Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide.

Authors:  Fu-Sheng He; Chun Zhang; Minghui Jiang; Lujun Lou; Jie Wu; Shengqing Ye
Journal:  Chem Sci       Date:  2022-07-08       Impact factor: 9.969

7.  Synthesis of New Morphinan Opioids by TBADT-Catalyzed Photochemical Functionalization at the Carbon Skeleton.

Authors:  Dmitry Gorbachev; Elliot Smith; Stephen P Argent; Graham N Newton; Hon Wai Lam
Journal:  Chemistry       Date:  2022-07-13       Impact factor: 5.020

8.  Carbene-catalyzed enantioselective annulation of dinucleophilic hydrazones and bromoenals for access to aryl-dihydropyridazinones and related drugs.

Authors:  Bivas Mondal; Rakesh Maiti; Xing Yang; Jun Xu; Weiyi Tian; Jia-Lei Yan; Xiangyang Li; Yonggui Robin Chi
Journal:  Chem Sci       Date:  2021-05-17       Impact factor: 9.825

9.  Enantioselective Synthesis of γ-Oxycarbonyl Motifs by Conjugate Addition of Photogenerated α-Alkoxy Radicals.

Authors:  Xiao Dong; Qi Yukki Li; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-07-23       Impact factor: 6.072

Review 10.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.