1,6-Addition of Tertiary Carbon Radicals Generated From Alcohols or Carboxylic Acids by Visible-Light Photoredox Catalysis

被引：45
作者：
Abbas, Samir Y. [1 ,2 ]
Zhao, Peng [1 ]
Overman, Larry E. [1 ]
机构：
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
[2] Natl Res Ctr, Organometall & Organometalloid Chem Dept, Cairo 12622, Egypt
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 03期
关键词：
STEREOGENIC CENTERS; ACTIVATED ALKENES; 1,3-DIENES;
D O I：
10.1021/acs.orglett.7b04034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The addition of tertiary carbon radicals generated by an Ir-catalyzed visible-light photocatalyst to electron-deficient 1,3-dienes proceeds in good yields to append a delta-substituted beta,gamma-unsaturated carbonyl fragment to a tertiary alcohol or carboxylic acid precursor and construct a new quaternary carbon center.
引用
收藏
页码：868 / 871
页数：4
相关论文
共 18 条
  • [1] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
    Chauhan, Pankaj
    Kaya, Ugur
    Enders, Dieter
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912
  • [2] Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin
    Chu, Lingling
    Ohta, Chisa
    Zuo, Zhiwei
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (31) : 10886 - 10889
  • [3] METHOD FOR STEREOSPECIFIC SYNTHESIS OF 1,3-DIENES AND 1,4-DIENES VIA ORGANOCOPPER REAGENTS
    COREY, EJ
    TAKEDA, M
    CHEN, RHK
    KIM, CU
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (12) : 4395 - &
  • [4] Conjugate addition reactions of carbon nucleophiles to electron-deficient dienes
    Csaky, Aurelio G.
    de la Herran, Gabriela
    Carmen Murcia, M.
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) : 4080 - 4102
  • [5] The persistent radical effect: A principle for selective radical reactions and living radical polymerizations
    Fischer, H
    [J]. CHEMICAL REVIEWS, 2001, 101 (12) : 3581 - 3610
  • [6] Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes
    Gong, Hegui
    Andrews, R. Stephen
    Zuccarello, Joseph L.
    Lee, Stephen J.
    Gagne, Michel R.
    [J]. ORGANIC LETTERS, 2009, 11 (04) : 879 - 882
  • [7] Hudlicky T., 2007, The Way of Synthesis - Evolution of Design and Methods for Natural Products
  • [8] One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine
    Liu, Xue-Kui
    Zheng, Xiao
    Ruan, Yuan-Ping
    Ma, Jie
    Huang, Pei-Qiang
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (06) : 1275 - 1284
  • [9] The reaction of fluorine-containing compounds with conjugated dienoic acids initiated by sodium dithionite
    Mao, Shengjie
    Fang, Xiang
    Ba, Lu
    Wu, Fanhong
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (01) : 5 - 11
  • [10] Constructing Quaternary Stereogenic Centers Using Tertiary Organocuprates and Tertiary Radicals. Total Synthesis of trans-Clerodane Natural Products
    Mueller, Daniel S.
    Untiedt, Nicholas L.
    Dieskau, Andre P.
    Lackner, Gregory L.
    Overman, Larry E.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) : 660 - 663
12