121741-99-9Relevant academic research and scientific papers
Diels-Alder reactions with dienes bearing a remote stereogenic center. Conformational model for diastereofacial selectivity
Siegel,Thornton
, p. 1413 - 1428 (2007/10/02)
In Diels-Alder reactions of 1-acyloxydienes, the 1-O-methylmandeloxy group has the distinct advantage of serving dual functions. Not only is it an effective chiral auxiliary for Diels-Alder stereocontrol, but also it provides rather reliable determination of the absolute stereochemistry of the Diels-Alder adduct, via the Dale-Mosher NMR model, subject only to the ability to resolve the proper NMR resonances. Study of the Diels-Alder reactions of such chiral 1-acyloxydienes has led us to a transition structure model which uniquely explains the origin of the observed stereoselectivities and is supported by experimental evidence, including X-ray structures showing the conformations of three Diels-Alder adducts. The model may also have wider applicability in conformational analysis and control of selectivity in other reactions.
CONFORMATIONAL MODEL FOR ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL DIENES
Siegel, Craig,Thornton, Edward R.
, p. 5225 - 5228 (2007/10/02)
1-(O-methylmandeloxy)dienes have significant advantages for asymmetric Diels-Alder reactions, and we now show that high (>90percent) diastereofacial selectivities can be obtained with these dienes, permitting considerable choice as to dienophile and the p
