The asymmetric C-H insertion of alkyldiazosulfones has been studied. High selectivity was achieved using a combination of a chiral catalyst and a chiral auxiliary (Rh2(S-pttl)4 and menthyl ester).
A highly efficient one-pot construction of optically active 1,1'-spirobi[indan-3,3'-dione] derivative (up to 80% ee) has been achieved by exploiting the double intramolecular C-H insertion reaction of dimethyl 2,2'-methylenebis(alpha-diazo-beta-oxobenzenepropanoate) under the influence of dirhodium(II) tetrakis[N-phthaloyl-(R or S)-tert-leucinate] as a catalyst.
An efficient and reliable procedure for the preparation of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh 2 (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.
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