Nickel-Catalyzed Ring-Opening Alkylative Coupling of Enone with Methylenecyclopropane in the Presence of Triethylborane

Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C–C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 15; no. 6; pp. 1182 - 1185
Main Authors Ogata, Kenichi, Shimada, Daisuke, Furuya, Shouichi, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALPHA-OLEFINS
(+)-ALLOPUMILIOTOXIN 267A
ENANTIOSELECTIVE SYNTHESIS
ALLYLIC ALCOHOLS
SILANES
REDUCTIVE COUPLINGS
ALDEHYDES
ALKYNES
SIMPLE ALKENES
CONJUGATE ADDITION
Online AccessGet full text

Cover

More Information
Summary:Nickel-catalyzed alkylative coupling of an enone or enal with methylenecyclopropane in the presence of triethylborane was achieved via stereospecific proximal C–C bond cleavage of methylenecyclopropane. With the use of methylenecyclopropane possessing an acyclic alkyl substituent, this reaction was also accompanied by the β-hydrogen elimination.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303548x