Catalytic Enantioselective Synthesis of Azepine-Fused Planar-Chiral Ferrocenes by Pt-Catalyzed Cycloisomerization

被引：21

作者：

Ito, Mamoru ^{[1
]}

Okamura, Moeka ^{[1
]}

Kanyiva, Kyalo Stephen ^{[2
]}

Shihata, Takanori ^{[1
]}

机构：

[1] Waseda Univ, Sch Adv Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

[2] Waseda Univ, Sch Adv Sci & Engn, Global Ctr Sci & Engn, Shinjuku Ku, 3-4-1 Okubo, Tokyo 1698555, Japan

来源：

ORGANOMETALLICS | 2019年 / 38卷 / 20期

关键词：

C-H ARYLATION; CYCLIC (AMINO)(FERROCENYL)CARBENE; CARBAMAZEPINE;

D O I：

10.1021/acs.organomet.9b00422

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective synthesis of azepine-fused planarchiral ferrocenes was achieved by the chiral cationic Pt-catalyzed intramolecular cycloisomerization of N-propargyl-2-ferrocenylanilines. A mechanistic study using an N-allenyl analogue indicated that the reaction proceeded selectively in a 7-exo-dig manner along with isomerization of the exo-olefin moiety. A methanesulfonylamino tether was crucial for selective cycloisomerization. This is the first example of the enantioselective synthesis of heteropin-fused planarchiral ferrocenes.

引用

页码：4029 / 4035

页数：7

共 50 条

[1] Pt-Catalyzed Enantioselective Cycloisomerization for the Synthesis of Planar-Chiral Ferrocene Derivatives
Shibata, Takanori
Uno, Ninna
Sasaki, Tomoya
Kanyiva, Kyalo Stephen
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6266 - 6272
[2] Asymmetric synthesis of planar-chiral ferrocenes by Mo- or Ru-catalyzed enantioselective metathesis
Ogasawara, Masamichi
Watanabe, Susumu
Nakajima, Kiyohiko
Takahashi, Tamotsu
[J]. PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1109 - 1113
[3] Kinetic resolution of planar-chiral ferrocenes by molybdenum-catalyzed enantioselective metathesis
Ogasawara, Masamichi
Watanabe, Susumu
Fan, Liyan
Nakajima, Kiyohiko
Takahashi, Tamotsu
[J]. ORGANOMETALLICS, 2006, 25 (22) : 5201 - 5203
[4] Enantioselective Staudinger synthesis of β-lactams catalyzed by a planar-chiral nucleophile
Hodous, BL
Fu, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1578 - 1579
[5] Insertion of carbenoids into Cp-H bonds of ferrocenes: An enantioselective-catalytic entry to planar-chiral ferrocenes
Siegel, S
Schmalz, HG
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22): : 2456 - 2458
[6] Enantioselective Synthesis of Ferrocene- or Cymantrene-Fused Planar-Chiral Phospholes
Hu, Hao
Wu, Wei-Yi
Takahashi, Tamotsu
Yoshida, Kazuhiro
Ogasawara, Masamichi
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (02) : 325 - 329
[7] Catalytic enantioselective synthesis of planar-chiral transition-metal complexes
Ogasawara, Masamichi
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[8] Mild access to planar-chiral ortho-condensed aromatic ferrocenes via gold(I)-catalyzed cycloisomerization of ortho-alkynylaryl ferrocenes
Urbano, Antonio
Hernandez-Torres, Gloria
del Hoyo, Ana M.
Martinez-Carrion, Alicia
Carreno, M. Carmen
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (38) : 6419 - 6422
[9] Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids
Hodous, BL
Ruble, JC
Fu, GC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) : 2637 - 2638
[10] Kinetic Resolution: A Powerful Tool for the Synthesis of Planar-Chiral Ferrocenes
Alba, Andrea-Nekane R.
Rios, Ramon
[J]. MOLECULES, 2009, 14 (11) : 4747 - 4757

← 1 2 3 4 5 →