Iron-catalyzed Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane

Authors
Carter, DS Van Vranken, DL
Citation
Ds. Carter et Dl. Van Vranken, Iron-catalyzed Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane, ORG LETT, 2(9), 2000, pp. 1303-1305
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
9
Year of publication
2000
Pages
1303 - 1305
Database
ISI
SICI code
1523-7060(20000504)2:9<1303:IDROAS>2.0.ZU;2-7
Abstract
Iron salts efficiently catalyze the Doyle-Kirmse reaction of allyl sulfides with (trimethylsilyl)diazomethane and ethyl diazoacetate in dichloroethane at 83 degrees C. Competitive dimerization is less of a problem with (trime thylsilyl)diazomethane than with ethyl diazoacetate. Good results are obtai ned using only 1.5 equiv of (trimethylsilyl)diazomethane, even without slow addition. Phosphine ligands affect the kinetics, but not the diastereosele ctivity. Dppe and BINAP lead to higher yields than dppp, but no enantiosele ction was detected with R-(+)-BINAP.