69016-40-6Relevant articles and documents
Stereoselective aziridination of cyclic allylic alcohols using chloramine-T
Coote, Susannah C.,O'Brien, Peter,Whitwood, Adrian C.
supporting information; experimental part, p. 4299 - 4314 (2009/02/07)
The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO 2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis- diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.
A sequential Claisen/ring-closing metathesis approach to the synthesis of spirocyclic cyclopentanes and cyclohexanes
Beaulieu, Patrick,Ogilvie, William W.
, p. 8883 - 8885 (2007/10/03)
A new method for the formation of spirocycles is described using a sequential Ireland-Claisen/Metathesis strategy to construct spirocyclic systems. Optimization of the Ireland-Claisen conditions provides the key metathesis substrates. The metathesis reactions were highly regioselective by virtue of steric hindrance in the substrate olefins.
