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Chiral aminocyclopentene-based cycloaddition strategies to bicyclic [3.3.0] rings |
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| Authors: | Chaozhong Cai Fu-An Kang Derek A Beauchamp Zhihua Sui Ronald K Russell Christopher A Teleha |
| Institution: | 1. Metabolic Diseases Research, Janssen Pharmaceutical Research and Development, Welsh and McKean Roads, PO Box 776, Spring House, PA 19477, USA;2. CREATe, High Output Synthesis Team (HOPS), Janssen Pharmaceutical Research and Development, Welsh and McKean Roads, PO Box 776, Spring House, PA 19477, USA |
| Abstract: | Two cycloaddition methods were applied to chiral protected aminocyclopentenes 2 and 9 and provided novel bicyclic products 3 and 4 in good yields. The explanation for the observed stereochemistry was based on the sterically encumbered β-face forcing the cycloadditions to occur on the α-face of the cyclopentene ring. The stereochemistry of 4 was confirmed by X-ray of the fumarate salt 10 and showed the trans-relationship between the newly formed ring and the chiral –NHBoc group. |
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