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

被引：29

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

页码：6324 / 6327

页数：4

共 55 条

[1] Highly enantioselective conjugate addition of thiols using mild scandium triflate catalysis [J].