Aluminum triflate catalyzed tandem reactions of D-galactal: toward chiral benzopyrans, chromenes, and chromans.

Publisher:
American Chemical Society
Publication Type:
Journal Article
Citation:
Organic Letters, 2014, 16 (17), pp. 4543 - 4545
Issue Date:
2014-09
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3,4,6-Tri-O-acetyl-D-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.
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