Journal
ORGANIC LETTERS
Volume 19, Issue 6, Pages 1306-1309Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00119
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- National Science Foundation [CHE-1464690]
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Chiral cyclopenta[2,3]cyclopropa[1,2-c]pyran-4-ones have been synthesized via dirhodium(II)-catalyzed intramolecular cyclopropanation of (Z)-1,3-dienyl aryldiazoacetates. High regio-, diastereo-, and enantiocontrol were achieved using chiral dirhodium 2-phthalimide carboxylates. Preferential addition occurs at the 3,4-rather than the 1,2-double bond with the chiral dirhodium catalysts, although both outcomes occur with other transition-metal catalysts.
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