Strain-Driven Direct Cross-Aldol and -Ketol Reactions of Four-Membered Heterocyclic Ketones

被引：13

作者：

Dobi, Zoltan ^{[1
]}

Holczbauer, Tamas ^{[1
]}

Soos, Tibor ^{[1
]}

机构：

[1] Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, H-1519 Budapest, Hungary

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 11期

关键词：

DRUG DISCOVERY; SUBSTITUTED OXETANES; 2+2 CYCLOADDITION; AMINO KETONES; AZETIDINES; OXETAN-3-ONES; DERIVATIVES; ALLENOATES; AZETIDIN-3-ONES; CYCLIZATION;

D O I：

10.1021/acs.orglett.5b01002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Owing to the ring strain and a-heteroatom effect, the four-membered heterocyclic ketones can undergo direct cross-aldol and -ketol reactions without the need for preformed enol or enolate-like intermediates. Besides the organocatalyzed cross-ketol addition onto their highly active carbonyl group, their ability to act as a nucleophilic donor has also been explored. As a result, a number of discrete aldol adducts were synthesized and the distinct reactivities were successfully combined into a double-aldol one-pot reaction.

引用

页码：2634 / 2637

页数：4

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