99216-76-9Relevant academic research and scientific papers
Asymmetric Hydrogenation Catalyzed by Rhodium Complex with a New Chiral Bisphosphine Derived from L-Threonine
Saito, Kunio,Saijo, Shigeyoshi,Kotera, Keishi,Date, Tadamasa
, p. 1342 - 1350 (2007/10/02)
A new chiral bisphosphine, (2R,3S)-1,2-bis(diphenylphosphino)-3-'Boc-aminobutane (RS-5), was prepared from L-threonine.Mesylation of 'Boc-L-threonine methyl ester (2) and subsequent reduction with sodium borohydride gave the alcohol (10), which was treated with potassium carbonate to afford a key intermediate, (2S,3S)-1-'Boc-3-methyl-2-aziridinemethanol (SS-7b).Mesylation of SS-7b, followed by treatment with sodium diphenylphosphide afforded the new chiral bisphosphine (RS-5).The structure of RS-5 was confirmed by the X-ray analysis of its crystalline CuCl complex (RS-12).The cationic rhodium (I) complexes prepared from RS-5 and RS-12 are efficient asymmetric hydrogenation catalysts for N-acyldehydroamino acids, giving (S))-N-acylamino acids in high optical yields (83-94percentee).
