ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION OF N-ALLYLIC AND N-HOMOALLYLIC DIAZOACETAMIDES CATALYZED BY CHIRAL DIRHODIUM(II) CATALYSTS

Authors
DOYLE MP EISMONT MY PROTOPOPOVA MN KWAN MMY
Citation
Mp. Doyle et al., ENANTIOSELECTIVE INTRAMOLECULAR CYCLOPROPANATION OF N-ALLYLIC AND N-HOMOALLYLIC DIAZOACETAMIDES CATALYZED BY CHIRAL DIRHODIUM(II) CATALYSTS, Tetrahedron, 50(15), 1994, pp. 4519-4528
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
15
Year of publication
1994
Pages
4519 - 4528
Database
ISI
SICI code
0040-4020(1994)50:15<4519:EICONA>2.0.ZU;2-N
Abstract
Diazodecomposition of N-(tert-butyl)-N-(3-buten-1-yl)diazoacetamides c atalyzed by dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxyla te], Rh-2(5S-MEPY)(4), and tetrakis[methyl 2-oxazolidinone-4(S)-carbox ylate], Rh-2(4S-MEOX)(4), forms products from intramolecular cycloprop anation in good yields with enantiomeric excesses ranging from 60-90%. Intramolecular cyclopropanation with N,N-diallyldiazoacetamide (72% e e) is competitive with intramolecular [3+2] dipolar cycloaddition.