Novel Synthesis of 3-Azabicyclo[3.1.0]hexanes by Unusual Palladium(0)-Catalyzed Cyclopropanation of Allenenes

Novel stereoselective synthesis of 3-azabicyclo[3.1.0]hexanes from allenenes is presented. Treatment of N-protected 4-alkyl-4-(N-allyl)amino allenes with allyl carbonate and a catalytic amount of Pd2(dba)3·CHCl3 in MeCN leads to stereoselective formation of the 3-azabicyclo[3.1.0]hexane framework in...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 5; no. 25; pp. 4763 - 4766
Main Authors Ohno, Hiroaki, Takeoka, Yusuke, Miyamura, Kumiko, Kadoh, Yoichi, Tanaka, Tetsuaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.12.2003
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
DIASTEREOSELECTIVE SYNTHESIS
HETEROCYCLES
DUOCARMYCINS
COUPLING-CYCLIZATION
AMINO
AZIRIDINATION
CONSTRUCTION
STEREOSELECTIVE-SYNTHESIS
CC-1065
Online AccessGet full text

Cover

More Information
Summary:Novel stereoselective synthesis of 3-azabicyclo[3.1.0]hexanes from allenenes is presented. Treatment of N-protected 4-alkyl-4-(N-allyl)amino allenes with allyl carbonate and a catalytic amount of Pd2(dba)3·CHCl3 in MeCN leads to stereoselective formation of the 3-azabicyclo[3.1.0]hexane framework in moderate to good yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0356441