Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates.
Dirhodium(II) tetrakis[ N-tetrachlorophthaloyl-( S)- tert-leucinate], Rh 2( S-TCPTTL) 4, is an exceptionally effective catalyst for enantioselective tandem carbonyl ylide formation-cycloaddition reactions of 2-diazo-3,6-diketoesters with arylacetylene, alkoxyacetylene, and styrene dipolarophiles, providing cycloadducts in good to high yields and with enantioselectivities of up to 99% ee as well as with perfect exo diastereoselectivity for styrenes.
Shimada
Naoyuki
N
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
Anada
Masahiro
M
Nakamura
Seiichi
S
Nambu
Hisanori
H
Tsutsui
Hideyuki
H
Hashimoto
Shunichi
S
D000480:Alkynes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
D000480:Alkynes; D001391:Azo Compounds; D002264:Carboxylic Acids; D004852:Epoxy Compounds; D004952:Esters; D007659:Ketones; D009942:Organometallic Compounds; D013343:Styrenes; D012238:Rhodium