Samarium diiodide mediated intramolecular cyclisation of mixed enone–enoate systems: a simple preparation of spirocyclic ethers

Meng, Junxiu; Light, Mark E.; Kilburn, Jeremy D.; Dixon, Sally

doi:10.1016/j.tetlet.2010.12.077

Cited by 4 publications

(2 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In general, the dimerization was found to proceed with high diastereoselectivity; however, mixtures of products were formed depending on the type of α,β-unsaturated acceptor. Kilburn and Dixon extended this study to the preparation of spirocyclic ethers (Scheme b) . The mechanism has been proposed to involve selective reduction of the cyclic β-alkoxyketone, followed by 5/6- exo -trig cyclization; however, it is possible that reduction of the acyclic ester occurs first, especially given that the reduction of β-heteroatom-substituted Michael acceptors using SmI 2 is known to be problematic (see section ).…”

Section: Cross-coupling Via Radical Intermediatesmentioning

confidence: 99%

“…Kilburn and Dixon extended this study to the preparation of spirocyclic ethers (Scheme 181b). 420 The mechanism has been proposed to involve selective reduction of the cyclic β-alkoxyketone, followed by 5/6-exo-trig cyclization; however, it is possible that reduction of the acyclic ester occurs first, especially given that the reduction of β-heteroatomsubstituted Michael acceptors using SmI 2 is known to be problematic (see section 3.1.2). This reaction provides an alternative method for the preparation of spirocyclic ethers with high diastereoselectivity.…”

Section: Cross-coupling Of Imines and Equivalentsmentioning

confidence: 99%

See 1 more Smart Citation