Rhodium-Catalyzed, Enantioselective Hydroacylation of ortho-Allylbenzaldehydes

被引：27
|
作者：
Johnson, Kirsten F. [1 ]
Schmidt, Adam C. [1 ]
Stanley, Levi M. [1 ]
机构：
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 19期
基金：
美国国家科学基金会;
关键词：
N-HETEROCYCLIC CARBENE; INTRAMOLECULAR HYDROACYLATION; HOMOGENEOUS CATALYSIS; REDUCTIVE ELIMINATION; CONVENIENT SYNTHESIS; BOND FORMATION; COMPLEXES; CASCADE; 4-PENTENALS; MECHANISM;
D O I：
10.1021/acs.orglett.5b02559
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The development of a rhodium catalyst for endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes is reported. A catalyst generated in situ from [Rh(COD)Cl](2), (R)-DTBM-SEGPHOS, and NaBARF promotes the desired hydroacylation reactions and minimizes the formation of byproducts from competitive alkene isomerization and ene/dehydration pathways. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in moderate-to-high yields (49-91%) with excellent enantioselectivities (96-99% ee).
引用
收藏
页码：4654 / 4657
页数：4
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