One-Pot Synthesis of Adamantane Derivatives by Domino Michael Reactions from Ethyl 2,4-Dioxocyclohexanecarboxylate

Adamantane derivatives were constructed by the one-pot reaction of ethyl 2,4-dioxocyclohexanecarboxylate with 2-phenylethyl 2-(acetoxymethyl)acrylate or 2-(acetoxymethyl)-1-phenyl-2-propen-1-one via domino Michael reactions and a Dieckmann condensation or an aldol-type reaction (four-bond formation)...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2005-10, Vol.70 (21), p.8587-8589
Main Authors: Takagi, Ryukichi, Miwa, Yukiko, Matsumura, Shuji, Ohkata, Katsuo
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Adamantane derivatives were constructed by the one-pot reaction of ethyl 2,4-dioxocyclohexanecarboxylate with 2-phenylethyl 2-(acetoxymethyl)acrylate or 2-(acetoxymethyl)-1-phenyl-2-propen-1-one via domino Michael reactions and a Dieckmann condensation or an aldol-type reaction (four-bond formation). This is the first one-pot construction of adamantane derivatives from cyclohexanone derivatives not involving enamines.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051163e