89293-98-1Relevant academic research and scientific papers
INVESTIGATION OF A CHIRAL MASKED KETENE SYNTHON. SYNTHESIS OF THE (+)-(1R,4R) and (-)-(1S,4S) ENANTIOMERS OF DEHYDRONORCAMPHOR
Maignan, Christian,Raphael, Ralph A.
, p. 3245 - 3250 (1983)
The Diels-Alder reaction between (+)-(R)-p-tolyl vinyl sulphoxide and cyclopentadiene gives four separable diastereoisomers.The two most abundant were transformed by a two-step procedure into the two enantiomers of dehydronorcamphor (bicyclohept-5-
Highly diastereoselective Diels-Alder reactions with (R)-ethoxy p-tolyl vinyl sulfonium tetrafluoroborate
Ronan, B.,Kagan, H. B.
, p. 75 - 90 (2007/10/02)
p-Tolyl vinyl sulfoxide has been efficiently activated for the Diles-Alder reactions by transformation into a sulfonium salt 3a or by addition of TMSOTf.Very high diastereomeric excesses have been achieved (>98percent) at -20 deg C in many cases.Best results have been obtained with cyclopentadiene, furan and 2,3-dimethyl-1,3-butadiene.In this way enantiomerically pure oxanorbornenone 19a has been prepared.The reaction mechanism is briefly discussed.
