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Complete Facial Selectivity in the Diels-Alder Reaction of a 5-Amino-5-carboxycyclopentadiene Derivative

TitleComplete Facial Selectivity in the Diels-Alder Reaction of a 5-Amino-5-carboxycyclopentadiene Derivative
Publication TypeJournal Article
Year of Publication2011
AuthorsKim, S, Ciufolini, MA
JournalORGANIC LETTERS
Volume13
Pagination3274-3277
Date PublishedJUN 17
ISSN1523-7060
Abstract

5-terf-Butoxycarbonylamino-5-carbethoxy-2-terf-butyldimethylsilyloxy-cyc lopentadiene undergoes a Diels Alder reaction exclusively from the face syn to the nitrogen functionality. Complete reversal of facial bias may be achieved, but at the cost of diminished reactivity, through steric shielding of the N-syn face.

DOI10.1021/ol201236j