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

被引：24

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.

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收藏

页码：4029 / 4035

页数：7

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