Meeting Challenges in Asymmetric Synthesis - Pharmaceutical Technology

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Meeting Challenges in Asymmetric Synthesis
Industry and academia advance novel approaches for achieving enanioselectivity.


Pharmaceutical Technology
Volume 36, Issue 9, pp. 48-50

Other catalytic approaches

BINOL and its derivatives are widely used classes of ligands in asymmetric synthesis, such as in Diels–Alder reactions, carbonyl addition, and reductions (7). Researchers at the University of Texas, Austin, recently developed a bifunctional catalyst derived from BINOL for producing highly enantioselective bromolactonizations of unsaturated carboxylic acids (8, 9). Specifically, the catalyst promoted highly enantioselective bromolactonizations of 4- and 5-aryl-4-pentenoic acids, but it also catalyzed the highly enantioselective bromolactonizations of 5-alkyl-4(Z)-pentenoic acids. The researchers assert that these reactions represent the first catalytic bromolactonizations of alkyl-substituted olefinic acids that proceeded by means of 5-exo mode cyclizations to give lactones in which new carbon–bromine bonds are formed at a stereogenic center with high enantioselectivity. The researchers also reported on what they say is the first catalytic desymmetrization of a prochiral dienoic acid by enantioselective bromolactonization (8, 9).

Patricia Van Arnum is executive editor of Pharmaceutical Technology, 485 Route One South, Bldg F, First Floor, Iselin, NJ 08830 tel. 732.346.3072,
twitter@PharmTechVArnum.

References

1 B. Halford, Chem. & Eng. News 90 (34), 9 (2012).

2. G. Coulthard, W. Erb, and K. Aggarwal, "Stereocontrolled Organocatalytic Synthesis of Prostagladin PGFin Seven Steps," Nature, online DOI10.1038/nature11411, Aug. 15, 2012.

3. M.J. Abrahamson, Angew. Chem. Int. Ed. Engl. 51 (16), 3969–3972 (2012).

4. T. Li et al., J. Am. Chem. Soc. 134 (14), 6467–6472 (2012).

5. P. Van Arnum, Pharm. Technol. 36 (5), 56–60 (2012).

6. B.M. Stoltz et al., Nature Chem. 4 (2) 130–133 (2012).

7. W. Sommer and D. Weibel, Aldrich ChemFiles 8.2 (56), 2008.

8. D.H. Paull, J. Am. Chem. Soc., 134 (27), pp 11128–11131 (2012).

9. C. Drahl, Chem. & Eng. News 90 (28), 29 (2012).


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