5436-03-3Relevant academic research and scientific papers
Heterodiene cycloadditoins of C2 symmetric 4,5-disubstituted ketene acetals: the nett asymmetric conjugate addition of recyclable acetic ester enolate equivalents to an activated enone
Wallace, Timothy W.,Wardell, Ian,Li, Ke-Dong,Leeming, Peter,Redhouse, Alan D.,Challand, S. Richard
, p. 2293 - 2308 (2007/10/02)
Heterodiene cycloadditions of 3-formylchromone 2 to a series of ketene acetals 1 derived from C2 symmetric 1,2-diarylethane-1,2-diols are diastereoselective.From (S,S)-1,2-di(o-tolyl)ethane-1,2-diol 6c the major cycloadduct 3c was isolated by crystallization and transformed by acid-catalysed methanolysis into (S)-methyl 4-oxo-3,4-dihydro-2H-1-benzopyran-2-ylacetate 5, together with the original 1,2-diol 6c which could be recycled.The structures of two cyclic carbonates 22a and 22c were determined by X-ray diffraction and used as models in seeking a mechanistic rationale for the stereoselective cycloadditions of the analogous ketene acetals 1a and 1c.
Preparation of racemic and enantiomerically pure cyclic ketene acetals
Diaz-Ortiz,Diez-Barra,De La Hoz,Prieto
, p. 1935 - 1942 (2007/10/02)
Cyclic ketene acetals have been prepared from a-haloaldehyde dimethylacetals by transacetalization and subsequent elimination in PTC without solvent conditions. No racemization has been observed when an enantiomerically pure diol has been used. Stability and storage conditions have been studies.
Nett Asymmetric Conjugate Addition of a Recyclable Acetic Ester Enolate Equivalent
Wallace, Timothy W.,Wardell, Ian,Li, Ke-Dong,Challand, S. Richard
, p. 1707 - 1708 (2007/10/02)
Heterodiene cycloadditions of 3-formyl chromone to ketene acetals derived from C2-symmetric 1,2-diarylethane-1,2-diols are diastereoselective; methanolysis of the cycloadducts derived from (S,S)-hydrobenzoin releases optically enriched methyl 3,4-dihydro-4-oxo-2H-1-benzopyran-2-ylacetate and the optically pure 1,2-diol.
