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Synthesis

Aldols On The Cheap

New version of the aldol reaction makes chiral alcohols inexpensively

by Carmen Drahl
July 15, 2013 | APPEARED IN VOLUME 91, ISSUE 28

To form carbon-carbon bonds with stereochemical control, chemists often turn to the aldol reaction, which forms chiral alcohols from two carbonyl compounds. Researchers have many options for this transformation, but new work suggests they could save money on it (Angew. Chem. Int. Ed. 2013, DOI: 10.1002/anie.201302535). William R. Roush of Scripps Research Institute Florida, who led the research, says he didn’t set out to find another variation on the aldol theme. His postdocs Philippe Nuhant and Christophe Allais chanced upon the chemistry while studying boron compounds derived from pinene, which other teams have previously used for aldol reactions. The process (shown) starts by combining the boron compounds with commercially available 4-acryloylmorpholine. By adding achiral or chiral aldehydes to the resulting intermediate, the team generates aldol products in the syn configuration. Then the morpholine moiety can be removed or altered. The whole process costs 20 cents per millimole, excluding waste disposal, Roush says, whereas most other options cost more because they require more steps or expensive catalysts. A route to anti configurations is in the works, but Roush has no plans to patent or commercialize the finding. He encourages chemists to try it—“no strings attached,” he says.

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