Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 49, Pages 15877-15880Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b11367
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Funding
- NIH [R01GM063540]
- NSF [CHE-1361296]
- JSPS KAKENHI [26.2447]
- Ermenegildo Zegna Group
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361296] Funding Source: National Science Foundation
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Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol.
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