103094-81-1Relevant articles and documents
Substituent effects in samarium diiodide-induced 6-trig cyclizations of γ-arylketones to functionalized hexahydronaphthalene derivatives
Berndt,Reissig
, p. 1290 - 1292 (2001)
The samarium diiodide-induced 6-trig cyclizations of substituted γ-arylketones 1, 4, 5, 9, 11, and 14 are strongly influenced by substituents of the aryl group. Whereas para-methoxy derivative 5 as well as ortho- and para-cyano derivatives 9 and 14 provided the expected functionalized hexahydronaphthalene derivatives 6 (together with 7), 10, and 15 in moderate to good yields, ortho-methoxy compound 1 was a poor substrate and meta-methoxy derivative 4 did not undergo cyclization at all. The behavior of meta-cyano compound 11 was exceptional since the intermediate cyclohexadienyl carbanion was sufficiently stable to be trapped by electrophiles furnishing adducts such as 17 and 18 in moderate yields.
Lewis Acid Mediated "endo-dig" Hydroalkoxylation-Reduction on Internal Alkynols for the Stereoselective Synthesis of Cyclic Ethers and 1,4-Oxazepanes
Gharpure, Santosh J.,Vishwakarma, Dharmendra S.,Nanda, Santosh K.
supporting information, p. 6534 - 6537 (2017/12/26)
Lewis acid mediated 5/6/7-endo-dig hydroalkoxylation-reduction cascade on internal alkynols gave an expedient, stereoselective synthesis of cyclic ethers and 1,4-oxazepanes. The strategy has been extended to the first examples of hydroalkoxylation-alkyne
Samarium diiodide mediated ketyl-aryl coupling reactions - Influence of substituents and trapping experiments
Wefelscheid, Ulrike K.,Berndt, Mathias,Reissig, Hans-Ulrich
experimental part, p. 3635 - 3646 (2009/06/06)
This comprehensive study describes the influence of substituents at the aryl moiety on SmI2-mediated intramolecular ketyl-aryl coupling reactions. Differently substituted γ-aryl ketones were employed as precursors, which were directly prepared
