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Catalytic asymmetric synthesis of new halogenated chiral synthons (1997)

Vanhessche, Koen P. M. ; Barry, K.

Weinheim : Wiley-Blackwell

Chemistry - A European Journal 3 (1997), S. 517-522

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ISSN: 0947-6539

Keywords: asymmetric catalysis ; chiral synthons ; cyclic sulfates ; dihydroxylations ; organofluorine compounds ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Two-step and practical asymmetric syntheses of enantiomerically pure 4-trifluoromethyl-2,2-dioxo-1,3,2-dioxathiolane and 4-trichloromethyl-2,2-dioxo-1,3,2-dioxathiolane (〉98% ee) have been achieved. Catalytic asymmetric dihydroxylation (AD) of 3,3,3-trifluoropropene and 3,3,3-trichloropropene, respectively, is followed by direct cyclic sulfate formation by reaction with sulfuryl chloride. Opening of the cyclic sulfates with various nucleophiles provides easy access to important chiral synthons.

Additional Material: 3 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/chem.19970030406

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