Chiral Organomagnesiates as Dual Reagents for Bromine-Magnesium Exchange of 2-Bromopyridine and Access to Chiral α-Substituted 2-Pyridylcarbinols

被引：25

作者：

Catel, Delphine ^{[1
]}

Chevallier, Floris ^{[2
]}

Mongin, Florence ^{[2
]}

Gros, Philippe C. ^{[1
]}

机构：

[1] Nancy Univ, CNRS, SRSMC, SOR, F-54506 Vandoeuvre Les Nancy, France

[2] Univ Rennes 1, CNRS, UMR 6510, F-35042 Rennes, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 01期

关键词：

Magnesium; Exchange reactions; Pyridylcarbinols; Chirality; Enantioselectivity; DIFFERENTIATING ASYMMETRIC ADDITION; ENANTIOSELECTIVE ADDITION; LITHIUM AMIDES; CARBONYL-COMPOUNDS; GRIGNARD-REAGENTS; PYRIDYL ALCOHOLS; ONE-STEP; ALDEHYDES; DIALKYLMAGNESIUM; ALKYLLITHIUM;

D O I：

10.1002/ejoc.201101490

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New chiral ligand containing butyl and dibutylmagnesiates have been prepared from a range of ligands and their reactivity studied. The reagents were generally efficient in promoting the clean bromine-magnesium exchange of 2-bromopyridine at room temperature and the subsequent reaction with aldehydes to afford alpha-substituted 2-pyridylcarbinols in good yields. (R,R)-TADDOLate proved to be the best ligand, leading to acceptable to good enantioselectivities. To the best of our knowledge this is the first example of an organomagnesiate-induced halogen-metal exchange followed by an enantioselective addition.

引用

页码：53 / 57

页数：5

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