Direct Synthesis of Highly Substituted 2-Cyclohexenones and Sterically Hindered Benzophenones Based on a [5C+1C] Annulation

被引：27

作者：

Fu, Zhenqian ^{[1
]}

Wang, Mang ^{[1
,2
]}

Dong, Ying ^{[1
]}

Liu, Jun ^{[1
]}

Liu, Qun ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 16期

关键词：

CATALYZED CARBONYLATIVE ANNULATION; MICHAEL ADDITION; KETENE DITHIOACETALS; O-IODOPHENOLS; REGIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTION; EFFICIENT SYNTHESIS; ACID-DERIVATIVES; INTERNAL ALKYNES; CYCLOHEXENONES;

D O I：

10.1021/jo9013386

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiospecific [5C + 1C] annulation of readily available alpha-alkenoyl ketene (S,S)-acetals 1 with aryl methyl ketones 2, the less active methylene compounds, has been developed. Upon treatment of 1 with 2 in the presence of t-BuOK in DMF at room temperature, highly substituted 2-cyclohexenones 3 were synthesized in high to excellent diastereoselectivities with high yields. Oil the basis of this strategy, stoically hindered benzophenones 4 Were conveniently prepared via the iodonation-aromatization of 2-cyclohexenones 3 With I-2 in MeONa/MeOH basic medium. Furthermore, benzopherones 4 Were also obtained directly from 1 and 2 following a sequential [5 + 1] annulation-iodonation-arormatization procedure in a one-pot operation.

引用

页码：6105 / 6110

页数：6

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