Synthesis of 2-indanones via [4+1] annulation reactions of (trialkylsilyl)arylketenes

被引：32

作者：

Dalton, AM ^{[1
]}

Zhang, YJ ^{[1
]}

Davie, CP ^{[1
]}

Danheiser, RL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 15期

关键词：

D O I：

10.1021/ol026014m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] (Trialkylsilyl)aryl ketenes combine with (trimethylsilyl)diazomethane in a new [4 + 1] annulation process leading to 2-indanone derivatives. The (trialkylsilyl)arylketene annulation substrates are available via the photochemical Wolff rearrangement of alpha-silyl-alpha-diazo ketones, which are themselves prepared by silylation of the corresponding diazo ketones. The mechanism of the annulation reaction is proposed to involve the formation of a 2,3-bis(silyl)cyclopropanone, which is in equilibrium with an oxyallylic cation. Electrocyclic closure of this intermediate forms the new cyclopentenone ring.

引用

页码：2465 / 2468

页数：4

共 32 条

[1] Hetero [4+2] cycloadditions of (trialkylsilyl)vinylketenes.: Synthesis of α,β-unsaturated δ-valerolactones and -lactams [J].