Asymmetric FeII-Catalyzed Thia-Michael Addition Reaction to α,β-Unsaturated Oxazolidin-2-one Derivatives

被引：28
|
作者：
Lauzon, Samuel [1 ]
Keipour, Hoda [1 ]
Gandon, Vincent [2 ,3 ]
Ollevier, Thierry [1 ]
机构：
[1] Univ Laval, Dept Chim, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
[2] Univ Paris Saclay, Univ Paris Sud, Inst Chim Mol & Mat Orsay, CNRS UMR 8182, F-91405 Orsay, France
[3] Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS UPR 2301, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 23期
基金：
加拿大自然科学与工程研究理事会;
关键词：
N-HETEROCYCLIC CARBENE; DIELS-ALDER ADDITION; S BOND FORMATION; CONJUGATE ADDITION; ALDOL REACTIONS; IRON CATALYSTS; C-H; THIOLS; COMPLEXES; CONSTRUCTION;
D O I：
10.1021/acs.orglett.7b03118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective Fe-II-catalyzed thia-Michael addition to alpha,beta-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding beta-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to alpha,beta-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantios elective event. DFT calculations support the proposed model for observed stereoselectivities.
引用
收藏
页码：6324 / 6327
页数：4
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