Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates

Citation
Hml. Davies et Rj. Townsend, Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates, J ORG CHEM, 66(20), 2001, pp. 6595-6603
Citations number
56
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
20
Year of publication
2001
Pages
6595 - 6603
Database
ISI
SICI code
0022-3263(20011005)66:20<6595:CACOH>2.0.ZU;2-6
Abstract
Rh-2(S-DOSP)(4)-catalyzed decomposition of heteroaryldiazoacetates in the p resence of styrene results in highly diastereoselective and enantioselectiv e cyclopropanations. Heteroaryldiazoacetates containing both electron-rich and electron-deficient heterocycles, such as thiophene, furan, pyridine, in dole, oxazole, isoxazole, and benzoxazole, are effective in this chemistry. These studies broaden the range of diazo compounds containing both electro n-withdrawing and electron-donating groups, which undergo highly diastereos elective cyclopropanations.