| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347686 | Tetrahedron: Asymmetry | 2013 | 6 Pages |
A series of Lewis bases were screened for Abramov-type phosphine additions to aldehydes. A novel phosphine oxide aziridinyl phosphonate POAP-A was found to be better than the others in forming the product in 96% yield and with 42% ee. The absolute configuration of the newly synthesized POAP Lewis bases was determined by single-crystal X-ray analysis.
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(R)-2-((R)-2-(Diethoxyphosphoryl)aziridin-1-yl)butyl 4-methylbenzenesulfonateC17H28NO6PS[α]D25=-12.5 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)
(R)-2-((S)-2-(Diethoxyphosphoryl)aziridin-1-yl)butyl 4-methylbenzenesulfonateC17H28NO6PS[α]D25=+44 (c 2.4, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)
Diethyl ((S)-1-((R)-1-(diphenylphosphoryl)butan-2-yl)aziridin-2-yl)phosphonateC22H31NO4P2[α]D25=+6.0(c 1.0, CH2Cl2)Source of chirality: asymmetric synthesis, X-ray analysisAbsolute configuration: (S,R)
Diethyl ((R)-1-((R)-1-(diphenylphosphoryl)butan-2-yl)aziridin-2-yl)phosphonateC22H31NO4P2[α]D25=-8.2(c 0.3, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,R)
