Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 9, Pages 3233-3236Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b00757
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Funding
- NIH [R01 GM078240, P50 GM067041]
- Dainippon Sumitomo Pharma Co., Ltd.
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM078240, P50GM067041] Funding Source: NIH RePORTER
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Tartaric acid is an ideal asymmetric catalyst as it is abundant, cheap, and environmentally friendly. (+)-Tartaric acid was found to catalyze a novel enantioselective [4 + 2] cycloaddition of isochromene acetals and vinylboronates. A variety of substituted isochromene acetals were tolerated, furnishing the desired dihydronaphthalenes and dihydrobenzofluorene products in good yields. High enantiomeric ratios (up to 98.5:1.5) and excellent diastereoselectivities (all >99:1) were observed employing 10 mol % of (+)-tartaric acid as the catalyst, in combination with 5 mol % of Ho(OTf)(3).
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