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- W2115430552 abstract "[180475-25-6] C21H28N3OP (MW 369.45)InChI = 1S/C21H28N3OP/c1-22-20(18-12-6-3-7-13-18)21(19-14-8-4-9-15-19)23(2)26(22,25)24-16-10-5-11-17-24/h3-4,6-9,12-15,20-21H,5,10-11,16-17H2,1-2H3/t20-,21-/m0/s1InChIKey = HZVXHACBRXLPRG-SFTDATJTSA-N(catalyst for asymmetric aldol additions of trichlorosilyl enolates to aldehydes,1 catalyst for asymmetric allylations and crotylations of allylic trichlorosilanes to aldehydes,2 catalyst for asymmetric ring opening of epoxides using silicon tetrachloride3)Physical Data: mp 110 °C; [α]D22 +18.2 (c=1.3, CHCl3).Solubility: soluble in most organic solvents except hydrocarbons.Form Supplied in: white needles.Preparative Methods: The enantiopure phosphoramide (S,S)-1a is prepared from treatment of (S,S)-N,N′-dimethyl-1,2-diphenyl-1,2-ethanediamine 5 with piperidinylphosphoric dichloride 6 and triethylamine (eq 1).4 Synthesis of related phosphoramides is easily accomplished by substituting the desired diamine backbone in the former procedure. Recrystallization of phosphoramide (S,S)-1a from hexane followed by drying over P2O5 allows for isolation of analytically pure material. Enantiopure 1,2-diphenyl-1,2-ethanediamine 5 can be prepared from benzil and cyclohexanone according to the method of Pikul & Corey.5 Bis-formylation of the diamine with acetic formic anhydride followed by LiAlH4 reduction affords N,N′-dimethyldiamine 5. Alternatively, enantiopure 5 can be prepared directly from benzaldehyde and methylamine according to the method of Alexakis et al.6 Piperidinylphosphoric dichloride 6 is prepared from piperidine, triethylamine and phosphorous oxychloride according to the modified procedure of Peyronel et al.7(1)Handling, Storage, and Precautions: The phosphoramide is a stable, hygroscopic compound which is best stored in a dessicator or dry-box. Avoid prolonged exposure to air or moisture." @default.
- W2115430552 created "2016-06-24" @default.
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- W2115430552 date "2002-04-15" @default.
- W2115430552 modified "2023-10-18" @default.
- W2115430552 title "[4S-(4α,5α)]-1-(1,3-Dimethyl-2-oxido-4,5-diphenyl-1,3,2-diazaphospholidine-2-yl)piperidine" @default.
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- W2115430552 doi "https://doi.org/10.1002/047084289x.rn00010" @default.
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