Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes Using Unsymmetrical Allylated Active Methine Radicals

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2607-2610

  Kitagawa, Osamu ^a   Miyaji, Shinsaku ^a   Sakuma, Chiseko ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; IODINE; OLEFINS; REACTION KINETICS;

METHINE RADICALS; STEREOSELECTIVE IODINE;

AROMATIC HYDROCARBONS;

1 DIETHYLPHOSPHONYL 2 (IODOMETHYL)CYCLOPROPANE 1 CARBOXYLIC ACID ETHYL ESTER; 1 PHENYLSULFONYL 2 (IODOMETHYL)CYLOPROPANE 1 CARBOXYLIC ACID METHYL ESTER; ALKENE; CYCLOPENTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; IODINE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 1842607534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035771a     Document Type: Article

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36. As described in our previous paper (ref 2a,b), in the reaction of dimethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate with 1-alkenes, moderate or relatively high 3,4-cis selectivity (5.6:1-11.2:1) between 3-iodomethyl and 4-alkyl groups has been observed.