Chiral phosphine oxide aziridinyl phosphonate as a Lewis base catalyst for enantioselective allylsilane addition to aldehydes

A series of chiral Lewis bases, phosphine oxide ferrocenyl aziridinyl methanol 1–4, phosphinyl aziridinyl phosphonates 5 and 6, and phosphine oxide aziridinyl phosphonates 7 and 8 were screened for allylsilane additions to aldehydes. Among the Lewis bases, 8 was found to catalyze the reaction by forming the product in up to 94% yield and with 77% ee.

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(S)-1-Phenyl-3-buten-1-olC10H12O[α]D25 = −17.1 (c 0.2, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(4-Nitrophenyl)-3-buten-1-olC10H11NO3[α]D25 = −30.9 (c 3.3, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(3-Nitrophenyl)-3-buten-1-olC10H11NO3[α]D25 = −19.8 (c 0.4, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(2-Methylphenyl)-3-buten-1-olC11H14O[α]D25 = −44.3 (c 1.2, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(3-Bromophenyl)-3-buten-1-olC10H11BrO[α]D25 = −41.6 (c 1.3, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(4-Methoxyphenyl)-3-buten-1-olC11H14O2[α]D25 = −6.8 (c 1.1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(4-Methylphenyl)-3-buten-1-olC11H14O[α]D25 = +5.0 (c 0.3, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(2-Naphthyl)-3-buten-1-olC14H14O[α]D25 = −23.6 (c 1.03, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(R)-1-(1-Naphthyl)-3-buten-1-olC14H14O[α]D25 = +7.1 (c 1.1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R)