Title | Complete Facial Selectivity in the Diels-Alder Reaction of a 5-Amino-5-carboxycyclopentadiene Derivative |
Publication Type | Journal Article |
Year of Publication | 2011 |
Authors | Kim, S, Ciufolini, MA |
Journal | ORGANIC LETTERS |
Volume | 13 |
Pagination | 3274-3277 |
Date Published | JUN 17 |
ISSN | 1523-7060 |
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. |
DOI | 10.1021/ol201236j |