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Artificial enzyme shows multiple selectivity

By Tetsuo Satoh |

Professor Kazuaki Ishigreo and colleagues at Nagoya University (Nagoya, Japan; http://en.nagoya-u.ac.jp) have shown that a chiral, supramolecular, U-shaped, boron Lewis acid catalyst (diagram) promotes the unprecedented multi-selective Diels–Alder reaction of propargyl aldehyde with cyclic dienes. The Diels–Alder reaction, which is a traditional [4 + 2] cycloaddition with two carbon–carbon bond formations, is one of the most powerful tools for synthesizing versatile and unique six-membered ring compounds. Independent from the substrate, enantio-, endo/exo-, π-facial-, regio-, site-, and substrate-selectivity could all be controlled by this U-shaped catalyst. The obtained reaction products could enable the concise synthesis of chiral diene ligands and a key intermediate of (+)-sarkomycin, an anti-tumor agent. The results are expected to contribute to the development of artificial enzyme-like supramolecular catalysts for multi-selective reactions, which will be able to target organic compounds that have thus far eluded synthesis.
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