Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.

Title Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.
Authors K.O. Marichev; J.T. Ramey; H. Arman; M.P. Doyle
Journal Org Lett
DOI 10.1021/acs.orglett.7b00119
Abstract

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.

Citation K.O. Marichev; J.T. Ramey; H. Arman; M.P. Doyle.Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates.. Org Lett. 2017. doi:10.1021/acs.orglett.7b00119

Related Elements

Rhodium

See more Rhodium products. Rhodium (atomic symbol: Rh, atomic number: 45) is a Block D, Group 9, Period 5 element with an atomic weight of 102.90550. Rhodium Bohr ModelThe number of electrons in each of Rhodium's shells is [2, 8, 18, 16, 1] and its electron configuration is [Kr] 4d8 5s1. The rhodium atom has a radius of 134 pm and a Van der Waals radius of 195 pm. Rhodium was discovered and first isolated by William Wollaston in 1804. In its elemental form, rhodium has a silvery white metallic appearance. Elemental RhodiumRhodium is a member of the platinum group of metals. It has a higher melting point than platinum, but a lower density. Rhodium is found in ores mixed with other metals such as palladium, silver, platinum, and gold. Rhodium is primarily used as the catalyst in the three-way catalytic converters of automobiles it is also highly valued in jewelry. The name Rhodium originates from the Greek word 'Rhodon,' which means rose.

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