Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 8, Pages 3066-3072Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900198b
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Funding
- NSF [CHE-0610349]
- NIH [R01 GM075107]
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[GRAPHICS] A three-step procedure for the synthesis of 2-arylpropionic acids (profens) from vinyl arenes in nearly enantiomerically pure form has been developed. Excellent yields (> 97%), regioselectivities (> 99%), and enantioselectivities (> 97% ee) for the desired branched products were obtained in the asymmetric hydrovinylation reactions of vinyl arenes, and the products from these reactions were transformed into 2-arylpropionic acids via oxidative degradation. Subsequent Curtius or Schmidt rearrangements of these acids provided highly valued 1-arylethyl amines, including a prototypical primary amine with an alpha-chiral tertiary N-alkyl group, in very good yields.
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