- Alkene Oxyamination Using Malonoyl Peroxides: Preparation of Pyrrolidines and Isoxazolidines
-
Treatment of homoallylic N-tosyl amines or allylic N-tosyl hydroxylamines with 1.5 equiv of a malonoyl peroxide provides a stereoselective method to access functionalized pyrrolidines and isoxazolidines. This metal free alkene oxyamination proceeds in 50-
- Alamillo-Ferrer, Carla,Curle, Jonathan M.,Davidson, Stuart C.,Lucas, Simon C. C.,Atkinson, Stephen J.,Campbell, Matthew,Kennedy, Alan R.,Tomkinson, Nicholas C. O.
-
p. 6728 - 6740
(2018/06/26)
-
- Convenient route to primary (Z)-allyl amines and homologs
-
A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)-geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C = C double bond in the deprotection with hydrazine was concomitantly observed. Copyright Taylor & Francis Group, LLC.
- Gerpe, Alejandra,Bollini, Mariela,Gonzalez, Mercedes,Cerecetto, Hugo
-
experimental part
p. 29 - 47
(2009/04/06)
-
- Aza- and oxacarbonylations of allyl phosphates catalyzed by rhodium carbonyl cluster. Selective synthesis of β,γ-unsaturated amides, esters, and acids
-
Rhodium-catalyzed carbonylation of allyl phosphates under CO (20 atm) at 50 deg C proceeds very efficiently in the presence of amines, alcohols, and water to give the corresponding β,γ-unsaturated amides, esters, and acids, respectively.These carbonylations occur with high regioselectivity at the less substituted carbon of allyl unit to give linear β,υ-unsaturated acid derivatives.
- Imada, Yasushi,Shibata, Ou,Murahashi, Shun-Ichi
-
p. 183 - 194
(2007/10/02)
-
- ANOMALOUS STEREOCHEMISTRY IN THE WITTIG REACTION INDUCED BY NUCLEOPHILIC GROUPS IN THE PHOSPHONIUM YLIDE
-
Reaction of ylides from 3-9 with benzaldehyde show that carboxylate and oxido functionalities proximate to the ylide center promote anomalously high E stereoselectivity in alkene formation.Through the use of α-deuterated ylides 12-14, an internal "trans-selective Wittig" mechanism was ruled out as a principal source of exaggerated E alkene production.
- Maryanoff, Bruce E.,Duhl-Emswiler, B. A.,Reitz, Allen B.
-
p. 187 - 190
(2007/10/02)
-