First application of tunable alkyl or aryl sulfinamides to the stereoselective synthesis of a chiral amine: asymmetric synthesis of (R)-didesmethylsibutramine ((R)-DDMS) using (R)-triethylmethylsulfinamide ((R)-TESA).

Zhengxu Han, Dhileepkumar Krishnamurthy, Derek Pflum, Paul Grover, Stephen A Wald, Chris H Senanayake

Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, MA 01752, USA.

Organic letters 2002 Nov 14

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A highly diastereoselective addition of i-BuLi to a triethylmethylsulfinamide derived aldimine was used as the key step in the first asymmetric synthesis of (R)-didesmethylsibutramine, a metabolite of sibutramine for the potential treatment of CNS disorders. [reaction: see text]

Citation

Zhengxu Han, Dhileepkumar Krishnamurthy, Derek Pflum, Paul Grover, Stephen A Wald, Chris H Senanayake. First application of tunable alkyl or aryl sulfinamides to the stereoselective synthesis of a chiral amine: asymmetric synthesis of (R)-didesmethylsibutramine ((R)-DDMS) using (R)-triethylmethylsulfinamide ((R)-TESA). Organic letters. 2002 Nov 14;4(23):4025-8