Construction of Complex 1,3-Cyclohexadienes via Phosphine-Catalyzed (4+2) Annulations of δ-Acetoxy Allenoates and Ketones

被引：28
|
作者：
Zhang, Yuwen [1 ]
Tong, Xiaofeng [1 ]
机构：
[1] Changzhou Univ, Jiangsu Key Lab Adv Catalyt Mat & Technol, Sch Petrochem Engn, 1 Gehu Rd, Changzhou 213164, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 19期
关键词：
DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; ENANTIOSELECTIVE SYNTHESIS; CARBON-CARBON; ALLENES; CYCLOADDITION; DERIVATIVES; CYCLOPENTENES; CYCLOHEXENES;
D O I：
10.1021/acs.orglett.7b02787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The phosphine-catalyzed substrate-dependent (4 + 2) annulations of delta-acetoxy allenoates with ketones is described. Allenoates 1 with an alkyl substituent at delta C are able to react with cyclic 1,3-diketones 2, wherein the delta C is attacked by the methenyl carbon of 2 while the alpha C attacks the ketone of 2. Allenoates 5 with an aryl group at delta C is poised to react with cyclic beta-carbonyl amides 6, in which the aC is attacked by the methenyl carbon of 6 and the delta C undergoes 1,2-addition to the ketone of 6.
引用
收藏
页码：5462 / 5465
页数：4
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