期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 35, 页码 12179-12181出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja104196x
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资金
- National Institute of General Medical Sciences [1R01GM079644]
- NSF [CHE-0649246]
Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 degrees C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate a-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be <9.9 kcal/mol.
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