500723-14-8Relevant articles and documents
Metal-Free Asymmetric Synthesis of Indanes through Chiral Hypervalent Iodine(III)-Mediated Ring Contraction
Ahmad, Anees,Silva, Luiz F.
, p. 2174 - 2181 (2016)
The iodine(III)-mediated asymmetric oxidative rearrangement of 1,2-dihydronaphthalenes was investigated to prepare optically active 1-substituted indanes. The chiral hypervalent iodine species is generated in situ from a chiral aryl iodide, prepared in 94% yield in one step. This metal-free protocol was applied to different cyclic alkenes, substituted with oxygen, with nitrogen, or at position 1 with aryl or methyl. Indanes can be isolated as an acetal or alcohol in up to 78% ee.
Highly enantioselective hydroformylation of aryl alkenes with diazaphospholane ligands
Watkins, Avery L.,Hashiguchi, Brian G.,Landis, Clark R.
scheme or table, p. 4553 - 4556 (2009/05/13)
(Chemical Equation Presented) Asymmetric, rhodium-catalyzed hydroformylation of terminal and internal aryl alkenes with diazaphospholane ligands is reported. Under partially optimized reaction conditions, high enantioselectivity (>90% ee) and regioselectivities (up to 65:1 α:β) are obtained for most substrates. For terminal alkenes, both enantioselectivity and regioselectivity are proportional to the carbon monoxide partial pressure, but independent of hydrogen pressure. Hydroformylation of para-substituted styrene derivatives gives the highest regioselectivity for substrates bearing electron-withdrawing substituents. A Hammett analysis produces a positive linear correlation for regioselectivity.
