Enantioselective synthesis of diverse sulfinamides and sulfinylferrocenes from phenylglycine-derived chiral sulfinyl transfer agent
A new chiral sulfinyl transfer auxiliary derived from readily available phenylglycine was developed. This auxiliary is utilized to synthesize a diverse array of alkyl- and arylsulfinamides and sulfinylferrocenes in high yields and excellent ee's. The desired products are produced in a one-pot sequence from the oxathiazolidine 2-oxide by two sequential nucleophilic additions that proceed in a stereospecific manner.
Han, Zhengxu S.,Meyer, Angelica M.,Xu, Yibo,Zhang, Yongda,Busch, Robert,Shen, Sherry,Grinberg, Nelu,Lu, Bruce Z.,Krishnamurthy, Dhileep,Senanayake, Chris H.
p. 5480 - 5484
(2011/08/09)
A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1,2,3-oxathiazolidme-2-oxide: Practical asymmetric synthesis of (R)-sibutramine
A novel and direct approach for the asymmetric synthesis of (R)-sibutramine via chiral amine 5 using N-tosyl-1,2,3-oxathiazolidine-2-oxide (13) as a recyclable chiral auxiliary is described. Chiral sulfinate imine 16e was obtained by treatment of 13e with
Han, Zhengxu,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
p. 327 - 333
(2012/12/22)
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