Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 17, Pages 6094-6097Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b02775
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Funding
- JSPS [26410108, 26293001, 14J08052]
- JST ACT-C [JPMJCR12YM]
- Grants-in-Aid for Scientific Research [26410108, 26293001, 14J08052] Funding Source: KAKEN
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Catalytic carboxylation of the allylic C-(sp(3))-H bond of terminal alkenes with CO2 was developed with the aid of a Co/Xantphos complex. A wide range of allylarenes and 1,4-dienes were successfully transformed into the linear styrylacetic acid and hexa-3,5-dienoic acid derivatives in moderate to high yields, with excellent regioselectivity. The carboxylation showed remarkable functional group tolerability, so that selective addition to CO2 occurred in the presence of other carbonyl groups such as amide, ester, and ketone. Since styrylacetic acid derivatives can be readily converted into optically active gamma-butyrolactones through Sharpless asymmetric dihydroxylation, this allylic C(sp(3))-H carboxylation showcases a facile synthesis of gamma-butyrolactones from simple allylarenes via short steps.
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