123878-29-5Relevant articles and documents
Stereoselective synthesis of eight-membered cyclic ethers by tandem Nicholas reaction/ring-closing metathesis: A short synthesis of (+)-cis-lauthisan
Ortega, Nuria,Martin, Tomas,Martin, Victor S.
, p. 871 - 873 (2006)
Cis-2,8-disubstituted oxocanes and the parent unsaturated precursors were prepared from the corresponding Co2(CO)6-cycloalkynic ethers. Key steps in such synthesis were the ether linkage formation by intermolecular Nicholas reaction, RCM of the suitable acyclic dienyl ether and montmorillonite K-10 induced isomerization of the complexed cycloalkyne. A short synthesis of (+)-cis-lauthisan taking advantage of the developed methodology is described.
Synthesis of α,α′-disubstituted linear ethers by an intermolecular nicholas reaction - Application to the synthesis of (+)-cis/-trans-lauthisan and (+)-cis/(+)-trans-obtusan
Ortega, Nuria,Martin, Tomas,Martin, Victor S.
scheme or table, p. 554 - 563 (2009/09/06)
A new and efficient methodology to prepare α,α'-disubstituted linear ethers through an intermolecular Nicholas reaction (interNR) is described. cis-2,8-Disubstituted oxocanes, cis-2,9-disubstituted oxonanes, their trans isomers, and their parent unsaturat
First synthesis of optically pure selenuranes and stereoselective alkaline hydrolysis. Their application to asymmetric [2,3] sigmatropic rearrangement of allylic selenoxides
Kurose, Noriyuki,Takahashi, Tamiko,Koizumi, Toru
, p. 12115 - 12129 (2007/10/03)
The first synthesis of optically pure selenuranes 1 has been accomplished by utilizing 2-exo-hydroxy-10 bornyl group as a chiral ligand Complete retention of the configuration has been observed in alkaline hydrolysis of 1 to give selenoxides 2. The structure of 1 and 2 has been fully established by X-ray crystallography. [2,3] Sigmatropic rearrangement of allylic selenoxides 2 gave the corresponding allylic alcohols 3 with up to 88% enantiomeric excess (ee). The [2,3] sigmatropic rearrangement of allylic selenoxides 2 progresses predominantly via an endo transition state.
