Dearomatizing anionic cyclizations of N-benzyl-N-methyldiphenylphosphinamides. Synthesis of gamma-(N-methylamino)phosphinic acids

Authors
Fernandez, I Ortiz, FL Tejerina, B Granda, SG
Citation
I. Fernandez et al., Dearomatizing anionic cyclizations of N-benzyl-N-methyldiphenylphosphinamides. Synthesis of gamma-(N-methylamino)phosphinic acids, ORG LETT, 3(9), 2001, pp. 1339-1342
Citations number
39
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
9
Year of publication
2001
Pages
1339 - 1342
Database
ISI
SICI code
1523-7060(20010503)3:9<1339:DACON>2.0.ZU;2-C
Abstract
[GRAPHICS] The first dearomatizing anionic reaction of a phenyl ring promoted by an N- benzyl-n-methylphosphinamide group is described, The intermediate lithium s pecies can be trapped with different electrophiles, affording tetrahydroben zo[c]-1-aza-2 lambda (6)-phospholes with excellent diastereoselectivity. Th e new process is a simple and very efficient entry to the stereoselective s ynthesis of functionalized gamma-(N-methylamino)phosphinic acids and esters .