Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 37, Pages 11950-11953Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b08515
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Chiral phosphoric acid-catalyzed asymmetric nitroso-Diels Alder reaction of nitrosoarenes with carbamate-dienes afforded cis-3,6-disubstituted dihydro-1,2-oxazines in high yields with excellent regio-, diastereo-, and enantioselectivities. Interestingly, we observed that the catalyst is able not only to control the enantioselectivity but also to reverse the regioselectivity of the noncatalyzed nitroso-Diels Alder reaction. The regiochemistry reversal and asynchronous concerted mechanism were confirmed by DFT calculations.
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