Regiocontrolled Iodoaminocyclization Reaction of an Ambident Nucleophile Mediated by Basic Metallic Reagent

A new and general method of iodine-mediated cyclization reactions of allyl or homoallyl carbamates, ureas, and amides was found to give N-cyclized products as single regioisomers. The present reaction proceeded in good yield through regiocontrol (N-cyclization > O-cyclization) and the increase in...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 21; pp. 7330 - 7335
Main Authors Fujita, Masao, Kitagawa, Osamu, Suzuki, Takashi, Taguchi, Takeo
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.10.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LACTAMS
IODOETHERIFICATION
STEREOSELECTIVE SYNTHESIS
1,3-ASYMMETRIC INDUCTION
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Summary:A new and general method of iodine-mediated cyclization reactions of allyl or homoallyl carbamates, ureas, and amides was found to give N-cyclized products as single regioisomers. The present reaction proceeded in good yield through regiocontrol (N-cyclization > O-cyclization) and the increase in the reactivity of an ambident nucleophile by a basic metallic reagent. The N-cyclization selectivity was remarkably affected by the additive employed. The iodoaminocyclization reaction of the homoallyl carbamates and ureas with a chiral center at the homoallylic position was found to proceed with high 1,3-cis- and 1,3-trans-selectivity, respectively.
Bibliography:ark:/67375/TPS-34HFVZ9T-L
istex:32C48D54582C84318F0724FDE51267E56E46EF60
Abstract published in Advance ACS Abstracts, October 1, 1997.
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo970898j