Indane-4-sulfonamide

Muller has explored enantioselective C-H insertion using optically active rhodium complexes, NsN=IPh as the oxidant, and indane 7 as a test substrate (Scheme 17.8) [35]. Chiral rhodium catalysts have been described by several groups and enjoy extensive application for asymmetric reactions with diazoalkanes ]46—48]. In C-H amination experiments, Pirrung s binaphthyl phosphate-derived rhodium system was found to afford the highest enantiomeric excess (31%) of the product sulfonamide 8 (20equiv indane 7, 71% yield). 

The amidation of saturated C—H bonds can be effectively catalyzed by ruthenium or manganese complexes. Unfunctionalized hydrocarbons, such as adamantane, cyclohexene, ethylbenzene, cumene, indane, tetralin, diphenylmethane and others, are selectively amidated with PhINTs in the presence of ruthenium or manganese porphyrins or the ruthenium cyclic amine complexes to afford N-substituted sulfonamides in 80-93% yields with high selectivity [807]. The enantioselective amidation of a C—H bond can be catalyzed by chiral (salen)manganese(III) complexes (e.g., 660) [808], or by chiral ruthenium(II) and manganese(III) porphyrins (Scheme 3.264) [809]. 

Indanone was prepared by chlorosulfonation of indane to give both the 4- and 5-positional isomers (2), which are difficult to separate. However, we could aminate the sulfonylchlorides and metallate the activated methylene of the 4-isomer in the mixture to give, upon quenching with oxygen, the indanol S2. This could be easily separated from any other products, in 25% yield from the sulfonamide mixture (Scheme XI). 

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