کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1314321 1499367 2012 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Regiospecific and diastereoselective aldol reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones: Asymmetric synthesis of tertiary trifluoromethyl allylic carbinols
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Regiospecific and diastereoselective aldol reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones: Asymmetric synthesis of tertiary trifluoromethyl allylic carbinols
چکیده انگلیسی

Regiospecific and diastereoselective aldol type reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones was reported, which affords the corresponding tertiary trifluoromethyl allylic carbinols in high yields with good diastereoselectivities (dr up to 90:10). The reduction of the condensation product 3a with LiBHEt3 and Catecholborane provides CF3-substituted syn- and anti-1,3-amino alcohols 5a and 5b in high yields with excellent diastereoselectivities (dr > 99:1).

Regiospecific and diastereoselective aldol type reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones was reported, which affords the corresponding tertiary trifluoromethyl allylic carbinols in high yields with good diastereoselectivities (dr up to 90:10).Figure optionsDownload as PowerPoint slideHighlights
► Regiospecific and diastereoselective aldol type reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones is described.
► The reaction tolerates a wide range of N-(tert-butanesulfinyl) ketimines and α,β-unsaturated trifluoromethyl ketones.
► The reaction provides a practical method for the asymmetric synthesis of tertiary trifluoromethyl allylic carbinols with good diastereoselectivities.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Fluorine Chemistry - Volume 133, January 2012, Pages 102–107
نویسندگان
, , ,