Dearomatizing Anionic Cyclizations of N-Benzyl-N-methyldiphenylphosphinamides. Synthesis of γ-(N-Methylamino)phosphinic Acids

The first dearomatizing anionic reaction of a phenyl ring promoted by an N-benzyl-N-methylphosphinamide group is described. The intermediate lithium species can be trapped with different electrophiles, affording tetrahydrobenzo[c]-1-aza-2λ5-phospholes with excellent diastereoselectivity. The new pro...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 3; no. 9; pp. 1339 - 1342
Main Authors Fernández, Ignacio, Ortiz, Fernando López, Tejerina, Baudilio, Granda, Santiago García
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2001
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
REAGENTS
NAPHTHALENES
MECHANISM
NUCLEOPHILIC-ADDITION
LITHIATION
AROMATIC CARBONYL-COMPOUNDS
ALUMINUM TRIS(2,6-DIPHENYLPHENOXIDE) ATPH
CONJUGATE ADDITION
ORGANOLITHIUMS
Online AccessGet full text

Cover

More Information
Summary:The first dearomatizing anionic reaction of a phenyl ring promoted by an N-benzyl-N-methylphosphinamide group is described. The intermediate lithium species can be trapped with different electrophiles, affording tetrahydrobenzo[c]-1-aza-2λ5-phospholes with excellent diastereoselectivity. The new process is a simple and very efficient entry to the stereoselective synthesis of functionalized γ-(N-methylamino)phosphinic acids and esters.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015716t