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Catalytic asymmetric synthesis of neolignan natural products (-)-epi-conocarpan and (+)-conocarpan has been achieved by exploiting an enantio- and diastereoselective intramolecular C-H insertion reaction to construct a cis-2-aryl-2,3-dihydrobenzofuran ring system as a key step. The C-H insertion reaction of 5-bromoaryldiazoacetate catalyzed by… (More)
An efficient and reliable procedure for the preparation of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)(4), a universally effective catalyst for a range of enantioselective carbene transformations, is described. The N-phthaloylation of (S)-tert-leucine by the method of Bose with essentially no racemization is a key to this process.
[figure: see text] A role of achiral oxazolidinones to enhance the enantioselectivity in reactions of N-cinnamoyloxazolidinones with alkyl radicals promoted by a chiral Lewis acid is described. Efficient enantioselective radical-mediated conjugate additions of N-cinnamoyloxazolidinone can be realized by use of a chiral zinc triflate generated from a readily… (More)
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… (More)