کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1345226 980186 2015 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enantioselective direct aldol reactions promoted by phosphine oxide aziridinyl phosphonate organocatalysts
ترجمه فارسی عنوان
واکنش آلدول مستقیم آلکالین به وسیله اکسید فسفین ایزادین آسپیدین فسفاته
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
چکیده انگلیسی

A series of phosphine oxide based chiral Lewis bases were screened as organocatalysts for silicon tetrachloride mediated direct asymmetric aldol reactions between cyclohexanone and various aromatic aldehydes. One of the phosphine oxide-aziridinyl phosphonate POAP-A Lewis bases formed the aldol products in up to 75% yield and with 65% ee.

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Diethyl ((R)-1-((S)-1-hydroxy-3-phenylpropan-2-yl)aziridin-2-yl)phosphonateC15H24NO4P[α]D33 = +28.0 (c 5.9, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

Diethyl ((S)-1-((S)-1-hydroxy-3-phenylpropan-2-yl)aziridin-2-yl)phosphonateC15H24NO4P[α]D34 = −57.6 (c 3.4, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

(S)-2-((R)-2-(Diethoxyphosphoryl)aziridin-1-yl)-3-phenylpropyl 4-methylbenzenesulfonateC22H30NO6PS[α]D34 = +25.7 (c 6.8, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S,R)

(S)-2-((S)-2-(Diethoxyphosphoryl)aziridin-1-yl)-3-phenylpropyl 4-methylbenzenesulfonateC22H30NO6PS[α]D34 = −7.6 (c 10.3, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

Diethyl ((R)-1-((S)-1-diphenylphosphoryl-3-phenylpropan-2-yl)aziridin-2-yl)phosphonateC27H33NO4P2[α]D34 = +16.6 (c 5.4, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (R,S)

Diethyl ((S)-1-((S)-1-(diphenylphosphoryl)-3-phenylpropan-2-yl)aziridin-2-yl)phosphonateC27H33NO4P2[α]D35 = +6.0 (c 7.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S,S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 26, Issue 23, 15 December 2015, Pages 1348–1353
نویسندگان
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