Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes

被引：118
作者：
Hao, Wei [1 ]
Wu, Xiangyu [1 ]
Sun, James Z. [1 ]
Siu, Juno C. [1 ]
MacMillan, Samantha N. [1 ]
Lin, Song [1 ]
机构：
[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 35期
关键词：
REDUCTIVE CYCLIZATION; MESO-AZIRIDINES; RING EXPANSION; STYRENYL AZIRIDINES; VINYL AZIRIDINES; COMPLEXES; EPOXIDES; OLEFINS; DESYMMETRIZATION; HETEROCYCLES;
D O I：
10.1021/jacs.7b06723
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes. This method provides an efficient approach to the synthesis of pyrrolidines, structural units prevalent in bioactive compounds and organocatalysts, from readily available starting materials. The overall redox-neutral reaction was achieved via a redox-relay mechanism, which harnesses radical intermediates for selective C-N bond cleavage and formation.
引用
收藏
页码：12141 / 12144
页数：4
相关论文
共 65 条
  • [1] A novel procedure for the synthesis of aziridines: application of Simmons-Smith reagents to aziridination
    Aggarwal, VK
    Stenson, RA
    Jones, RVH
    Fieldhouse, R
    Blacker, J
    [J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1587 - 1589
  • [2] REGIOSPECIFIC METAL-CATALYZED RING EXPANSION OF AZIRIDINES TO BETA-LACTAMS
    ALPER, H
    URSO, F
    SMITH, DJH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) : 6737 - 6738
  • [3] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines
    Arai, Kenzo
    Lucarini, Simone
    Salter, Matthew M.
    Ohta, Kentaro
    Yamashita, Yasuhiro
    Kobayashi, Shuj
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) : 8103 - 8111
  • [4] THE FIRST ENANTIOSPECIFIC PALLADIUM-CATALYZED CYCLOADDITION OF AZIRIDINES AND HETEROCUMULENES - NOVEL SYNTHESIS OF CHIRAL 5-MEMBERED RING HETEROCYCLES
    BAEG, JO
    BENSIMON, C
    ALPER, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) : 4700 - 4701
  • [5] Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin
    Beaumont, Stephane
    Ilardi, Elizabeth A.
    Monroe, Lucas R.
    Zakarian, Armen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1482 - +
  • [6] Synthesis of bicyclic proline analogs using a formal [3+2] intramolecular aziridine-allylsilane cycloaddition reaction
    Bergmeier, SC
    Fundy, SL
    Seth, PP
    [J]. TETRAHEDRON, 1999, 55 (26) : 8025 - 8038
  • [7] Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five-Membered Heterocycles
    Cardoso, Ana L.
    Pinho e Melo, Teresa M. V. D.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (33) : 6479 - 6501
  • [8] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate
    Catino, AJ
    Nichols, JM
    Forslund, RE
    Doyle, MP
    [J]. ORGANIC LETTERS, 2005, 7 (13) : 2787 - 2790
  • [9] Titanium Enolate Chemistry at the Beginning of the 21st Century
    Ciez, Dariusz
    Palasz, Aleksandra
    Trzewik, Bartosz
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (08) : 1476 - 1493
  • [10] TITANIUM-CATALYZED REDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES AND ALDEHYDES
    CROWE, WE
    RACHITA, MJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (25) : 6787 - 6788
1234567