A New Powerful Strategy for the Organocatalytic Asymmetric Construction of a Quaternary Carbon Stereogenic Center

被引：53
|
作者：
Inokoishi, Yogo [1 ]
Sasakura, Niiha [1 ]
Nakano, Keiji [1 ]
Ichikawa, Yoshiyasu [1 ]
Kotsuki, Hiyoshizo [1 ]
机构：
[1] Kochi Univ, Fac Sci, Lab Nat Prod Chem, Akebono, Kochi 7808520, Japan
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 07期
关键词：
ENANTIOSELECTIVE CONJUGATE ADDITION; MICHAEL ADDITION; KETONES; AMINE; ALDEHYDES;
D O I：
10.1021/ol100350w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for chiral diamine-catalyzed Robinson-type annulation was developed to construct cyclohexenone derivatives bearing a quaternary carbon stereogenic center at the 4-position In high enantiomeric excess. This method was successfully applied to the short synthesis of (+)-sporochnol A.
引用
收藏
页码：1616 / 1619
页数：4
相关论文
共 50 条
  • [1] Catalytic Asymmetric Conjugate Addition of α-Cyanoketones for the Construction of a Quaternary Stereogenic Center
    Kawato, Yuji
    Takahashi, Noriko
    Kumagai, Naoya
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2010, 12 (07) : 1484 - 1487
  • [2] New allylic alkylation reactions: Asymmetric construction of acyclic quaternary carbon stereogenic centers
    Evans, P. Andrew
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [3] Synthesis of β-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions
    Mase, N
    Tanaka, F
    Barbas, CF
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2420 - 2423
  • [4] Organocatalytic asymmetric desymmetrization: efficient construction of spirocyclic oxindoles bearing a unique all-carbon quaternary stereogenic center via sulfa-Michael addition
    Yao, Lu
    Liu, Kang
    Tao, Hai-Yan
    Qiu, Guo-Fu
    Zhou, Xiang
    Wang, Chun-Jiang
    CHEMICAL COMMUNICATIONS, 2013, 49 (54) : 6078 - 6080
  • [5] Quaternary stereogenic carbon atoms in complex molecules by an asymmetric, organocatalytic, triple-cascade reaction
    Penon, Oriol
    Carlone, Armando
    Mazzanti, Andrea
    Locatelli, Manuela
    Sambri, Letizia
    Bartoli, Giuseppe
    Melchiorre, Paolo
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4788 - 4791
  • [6] Construction of a quaternary stereogenic center by asymmetric hydroformylation: a straightforward method to prepare chiral α-quaternary amino acids
    Zhang, Dequan
    Wen, Jialin
    Zhang, Xumu
    CHEMICAL SCIENCE, 2022, 13 (24) : 7215 - 7223
  • [7] Noncovalent Organocatalytic Synthesis of Enantioenriched Terminal Aziridines with a Quaternary Stereogenic Center
    De Fusco, Claudia
    Fuoco, Tiziana
    Croce, Gianluca
    Lattanzi, Alessandra
    ORGANIC LETTERS, 2012, 14 (16) : 4078 - 4081
  • [8] Diastereoselective ring-closing metathesis for the construction of a quaternary carbon stereogenic center
    Fukuda, Y
    Sasaki, H
    Shindo, M
    Shishido, K
    TETRAHEDRON LETTERS, 2002, 43 (11) : 2047 - 2049
  • [9] Asymmetric Organocatalytic Synthesis of β-Hydroxyynones with a Quaternary Carbon Center under Aqueous Conditions
    Kang, Guowei
    Jiang, Jun
    Liu, Hongxin
    Wu, Huayue
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (01) : 5 - S26
  • [10] Construction of an Asymmetric Quaternary Carbon Center via Allylation of Hydrazones
    Kim, Jin Bum
    Satyender, Apuri
    Jang, Doo Ok
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (11): : 3185 - 3186
12345