کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1349576 980405 2009 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Amino thiols versus amino alcohols in the asymmetric alkynylzinc addition to aldehydes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Amino thiols versus amino alcohols in the asymmetric alkynylzinc addition to aldehydes
چکیده انگلیسی

A series of modular amino thiol and amino alcohol ligands have been synthesized in enantiopure form from common enantiopure precursors. Their structures have been optimized for performance in the asymmetric alkynylzinc addition to aldehydes, and a direct comparison of the effect of the S and O coordinating atoms on the catalytic outcome of these ligands has been performed. Amino thiols have shown to be superior as ligands for this type of chemistry.

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(1S,2R)-1-Phenyl-2-(piperidin-yl)-3(trityloxy)propane-1-thiolC33H35NOSEe = 100%[α]D20=+52.7 (c 2.1, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-3-Methoxy-1-phenyl-2-(piperidin-1-yl)propane-1-thiolC15H23NOSEe = 100%[α]D20=+179.7 (c 0.27, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-2-(Dimethylamino)-1-phenyl-3-(trityloxy)propane-1-thiolC30H31NOSEe = 100%[α]D20=+35.8 (c 0.45, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-2-(Dimethylamino)-3-methoxy-1-phenylpropane-1-thiolC12H19NOSEe = 100%[α]D20=+97.7 (c 3.4, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-1-Phenyl-2-(piperidin-1-yl)-3-(trityloxy)propan-1-olC33H35NO2Ee = 100%[α]D20=+3.1 (c 0.84, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-2-(Dimethylamino)-1-phenyl-3-(trityloxy)propan-1-olC30H31NO2Ee = 100%[α]D20=+35.8 (c 0.45, CHCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

(1S,2R)-2-(Dimethylamino)-3-methoxy-1-phenylpropan-1-olC12H19NO2Ee = 100%[α]D20=+16.7 (c 0.55, CDCl3)Source of chirality: (S,S)-phenylglycidolAbsolute configuration: (1S,2R)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 12, 2 July 2009, Pages 1413–1418
نویسندگان
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