Catalytic enantioselective synthesis of quaternary carbon stereocentres

被引:817
作者
Quasdorf, Kyle W. [1 ]
Overman, Larry E. [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
基金
美国国家卫生研究院;
关键词
ASYMMETRIC CONJUGATE ADDITION; SUBSTITUTED CYCLIC ENONES; ARYL ALUMINUM REAGENTS; DIELS-ALDER REACTIONS; TRISUBSTITUTED ENONES; ALLYLIC ALKYLATION; STEREOGENIC CENTERS; INTRAMOLECULAR ARYLCYANATION; POLYENE CYCLIZATION; OLEFIN METATHESIS;
D O I
10.1038/nature14007
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Quaternary carbon stereocentres-carbon atoms to which four distinct carbon substituents are attached-are common features of molecules found in nature. However, before recent advances in chemical catalysis, there were few methods of constructing single stereoisomers of this important structural motif. Here we discuss the many catalytic enantioselective reactions developed during the past decade for the synthesis of single stereoisomers of such organic molecules. This progress now makes it possible to incorporate quaternary stereocentres selectively in many organic molecules that are useful in medicine, agriculture and potentially other areas such as flavouring, fragrances and materials.
引用
收藏
页码:181 / 191
页数:11
相关论文
共 98 条
  • [51] Scalable enantioselective total synthesis of taxanes
    Mendoza, Abraham
    Ishihara, Yoshihiro
    Baran, Phil S.
    [J]. NATURE CHEMISTRY, 2012, 4 (01) : 21 - 25
  • [52] Nucleophile-catalyzed asymmetric acylations of silyl ketene imines: Application to the enantioselective synthesis of verapamil
    Mermerian, AH
    Fu, GC
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) : 949 - 952
  • [53] Catalytic Asymmetric Total Synthesis of Chimonanthine, Folicanthine, and Calycanthine through Double Michael Reaction of Bisoxindole
    Mitsunuma, Harunobu
    Shibasaki, Masakatsu
    Kanai, Motomu
    Matsunaga, Shigeki
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5217 - 5221
  • [54] Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones
    Mueller, Daniel
    Alexakis, Alexandre
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (45) : 15226 - 15239
  • [55] Intramolecular arylcyanation of alkenes catalyzed by nickel/AlMe2CI
    Nakao, Yoshiaki
    Ebata, Shiro
    Yada, Akira
    Hiyama, Tamejiro
    Ikawa, Masashi
    Ogoshi, Sensuke
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) : 12874 - +
  • [56] New Chemical Entities Entering Phase III Trials in 2012
    Notte, Gregory T.
    [J]. ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 48, 2013, 48 : 451 - 469
  • [57] Ohmatsu K, 2014, NAT CHEM, V6, P47, DOI [10.1038/NCHEM.1796, 10.1038/nchem.1796]
  • [58] Recent developments in asymmetric cyclopropanation
    Pellissier, Helene
    [J]. TETRAHEDRON, 2008, 64 (30-31) : 7041 - 7095
  • [59] 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
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4788 - 4791
  • [60] Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation
    Phan, Diem H. T.
    Kou, Kevin G. M.
    Dong, Vy M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) : 16354 - 16355