[読みたい論文] 光学活性亜鉛触媒によるエナンチオ選択的分子内Conia-ene型反応

Viewed: 19:55:10 in December 11, 2019

Posted: March 15, 2019

[J. Am. Chem. Soc. 2019, 141 (10), 4199−4203] Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst (Cao, Min; Yesilcimen, Ahmet; Wasa, Masayuki)

Keywords: Conia-ene reaction; Zn; B(C6F5)3; BOx

不斉亜鉛触媒存在下での、炭素−炭素三重結合を持つケトンのエナンチオ選択的環化について報告しているようです。


この論文の反応で使われているケトン、カルボニル基の隣の炭素に不斉中心があるのですが、Conia-ene反応ではケトンのエノール化によってそこの不斉中心がなくなるので、出発化合物がラセミ体であってもあまり気にしなくて良い、ということなのでしょう。もしかしたら速度論的な光学分割、つまり、どちらかの鏡像体が優先して反応して行くのかもしれませんが。

さて、論文のタイトルについて気になることがありました。Conia-ene反応、下のようなものなのですが、


この論文のGraphical Abstractに書いてある化合物からだと、4員環の化合物が生成するのではと思うのですよね。どこがどう違って5員環のものができるのでしょうか。


その辺りのことを知りたいので、読みたい論文に追加です。Conia-Ene-"Type"反応とあしますし、アミン塩基がありますので、エノール化ではなくエノラートアニオンとなって分子内のアルキンに付加、そのあとプロトン化、なのかもしれません。

この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
twitterアカウントは@makiokafufudo(お仕事用)、@ymakioka(個人用)です。

 

1942年はこんな年

人名反応など
Wittig転位
ノーベル化学賞
(該当者なし)

できごと
興亜工業大学(現千葉工業大学)開校
帝国石油設立
鉄道技術研究所設立
西日本鉄道(西鉄)設立
広島電鉄設立。
三井船舶(商船三井)設立
関門鉄道トンネル開業
大日本映画(大映)設立
産業経済新聞(産経新聞)創刊
西日本新聞発刊
静岡新聞創刊
東京新聞創刊
東京に初の空襲警報発令
井の頭自然文化園開園
共栄火災海上保険設立

 

きょうのどうぶつ

ここの画像を使用しています。

近所の松の木をつついているコゲラ。

 

あわせてどうぞ

SOHOのすすめ記事一覧 2019年
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