| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344529 | Tetrahedron: Asymmetry | 2010 | 6 Pages |
On the basis of the phenomenon of self-assembly catalysis, a tridentate ligand was designed and synthesized in two steps. The application in alkynylation of N-(diphenylphosphinoyl) imines gave the expected products. Aromatic, heteroaromatic N-(diphenylphosphinoyl) imines were employed and gave optically active propargylic amines in good yields (up to 89%) and excellent enantioselectivities (up to 96%) by a simple experimental procedure. The direct use of sulfone amides in the alkynylation of N-(diphenylphosphinoyl) aliphatic imines made this method very attractive.
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(S)-(1-(Pyridin-2-ylmethyl)pyrrolidin-2-yl)methanolC11H16N2O[α]D20=-83 (c 0.4, CHCl3)Chirality source: l-prolineAbsolutely configuration: (S)
(S)-(1-(Furan-2-ylmethyl)pyrrolidin-2-yl)methanolC10H15NO2[α]D20=-88 (c 0.5, CHCl3)Chirality source: l-prolineAbsolutely configuration: (S)
(S)-(1-(Thiophen-2-ylmethyl)pyrrolidin-2-yl)methanolC10H15NOS[α]D20=-83 (c 0.5, CHCl3)Chirality source: l-prolineAbsolutely configuration: (S)
(S)-N-(1,3-Diphenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H22NOP[α]D20=-92 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(3-phenyl-1-p-tolylprop-2-ynyl)phosphinic amideC28H24NOP[α]D20=-79 (c 1.2, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Methoxyphenyl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC28H24NO2P[α]D20=-62 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Fluorophenyl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H21FNOP[α]D20=-63 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Chlorophenyl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H21ClNOP[α]D20=-63 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Bromophenyl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H21BrNOP[α]D20=-72 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(3-Chlorophenyl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H21ClNOP[α]D20=-48 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(Naphthalen-2-yl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC31H24NOP[α]D20=-41 (c 0.7, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(3-phenyl-1-(thiophen-2-yl)prop-2-ynyl)phosphinic amideC25H20NOPS[α]D20=-72 (c 1.0, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(1-phenyl-3-(thiophen-2-yl)prop-2-ynyl)phosphinic amideC25H20NOPS[α]D20=-82 (c 0.48, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(3-(thiophen-2-yl)-1-p-tolylprop-2-ynyl)phosphinic amideC26H22NOPS[α]D20=-74 (c 0.45, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Methoxyphenyl)-3-(thiophen-2-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC26H22NO2PS[α]D20=-97 (c 0.44, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Fluorophenyl)-3-(thiophen-2-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC25H19FNOPS[α]D20=-65 (c 0.52, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Chlorophenyl)-3-(thiophen-2-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC25H19ClNOPS[α]D20=-68 (c 0.5, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Bromophenyl)-3-(thiophen-2-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC25H19BrNOPS[α]D20=-70 (c 0.5, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(3-(thiophen-2-yl)-1-(thiophen-3-yl)prop-2-ynyl)phosphinic amideC23H18NOPS2[α]D20=-78 (c 0.5, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(1-phenyl-3-(thiophen-3-yl)prop-2-ynyl)phosphinic amideC25H20NOPS[α]D20=-73 (c 0.6, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Methoxyphenyl)-3-(thiophen-3-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC26H22NO2PS[α]D20=-42 (c 0.36, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-(4-Fluorophenyl)-3-(thiophen-3-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC25H19FNOPS[α]D20=-77 (c 0.8, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(R)-P,P-Diphenyl-N-(1-(thiophen-2-yl)-3-(thiophen-3-yl)prop-2-ynyl)phosphinic amideC23H18NOPS2[α]D20=-59 (c 0.8, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (R)
(S)-N-(4-Methyl-1-phenylpent-1-yn-3-yl)-P,P-diphenylphosphinic amideC24H2 4NOP[α]D20=-68 (c 0.5, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-Cyclohexyl-3-phenylprop-2-ynyl)-P,P-diphenylphosphinic amideC27H28NOP[α]D20=-55 (c 0.5, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(1-phenylnon-1-yn-3-yl)phosphinic amideC27H30NOP[α]D20=-50 (c 0.8, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(4-Methyl-1-(thiophen-2-yl)pent-1-yn-3-yl)-P,P-diphenylphosphinic amideC22H22NOPS[α]D20=-107 (c 0.3, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-Cyclohexyl-3-(thiophen-2-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC25H26NOPS[α]D20=-69 (c 0.4, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(1-(thiophen-2-yl)hex-1-yn-3-yl)phosphinic amideC22H22NOPS[α]D20=-36 (c 0.3, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-P,P-Diphenyl-N-(1-(thiophen-2-yl)non-1-yn-3-yl)phosphinic amideC25H28NOPS[α]D20=-42 (c 0.36, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)
(S)-N-(1-Cyclohexyl-3-(thiophen-3-yl)prop-2-ynyl)-P,P-diphenylphosphinic amideC22H22NOPS C25H28NOPS[α]D20=-81 (c 0.44, CHCl3)Chirality source: asymmetric alkynylation reactionAbsolutely configuration: (S)2 Molecular formulae, and the structure is the same as (S)-N-(4-methyl-1-(thiophen-2-yl)pent-1-yn-3-yl)-P,P-diphenylphosphinic amide[α]D20=-107 (c 0.3, CHCl3)
