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

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journal contribution
posted on 17.06.2011, 00:00 by Simon Kim, Marco A. Ciufolini
5-tert-Butoxycarbonylamino-5-carbethoxy-2-tert-butyldimethylsilyloxy-cyclopentadiene 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.