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
相关论文
共 50 条
  • [1] Rhodium-catalyzed enantioselective intermolecular hydroacylation reactions
    Gonzalez-Rodriguez, Carlos
    Willis, Michael C.
    PURE AND APPLIED CHEMISTRY, 2011, 83 (03) : 577 - 585
  • [2] Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes
    Schmalz, Veronika
    Koert, Ulrich
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (23) : 5870 - 5875
  • [3] Rhodium-Catalyzed Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes
    Johnson, Kirsten F.
    Schneider, Eugene A.
    Schumacher, Brian P.
    Ellern, Arkady
    Scanlon, Joseph D.
    Stanley, Levi M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (44) : 15619 - 15623
  • [4] RHODIUM-CATALYZED HYDROACYLATION - A MECHANISTIC PROBE
    GABLE, KP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 554 - ORGN
  • [5] Rhodium-catalyzed intermolecular ketone hydroacylation
    Schenthal, Kyle B.
    Kou, Kevin G. M.
    Dong, Vy M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [6] Phthalides by Rhodium-Catalyzed Ketone Hydroacylation
    Phan, Diem H. T.
    Kim, Byoungmoo
    Dong, Vy M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15608 - +
  • [7] Substitution effects in rhodium-catalyzed intramolecular hydroacylation
    Schneider, Eugene
    Scanlon, Joseph
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [8] Enantioselective rhodium-catalyzed hydroacylation to access the four stereoisomers of anti-rodent difenacoum
    Jacolot, Maiwenn
    Moebs-Sanchez, Sylvie
    Popowycz, Florence
    TETRAHEDRON LETTERS, 2017, 58 (16) : 1636 - 1639
  • [9] Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of -Aryl Ketones
    Bouisseau, Anais
    Gao, Ming
    Willis, Michael C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (44) : 15624 - 15628
  • [10] An enamine controlling group for rhodium-catalyzed intermolecular hydroacylation
    Straker, Robert N.
    Formica, Michele
    Lupton, James D.
    Niu, Jingze
    Willis, Michael C.
    TETRAHEDRON, 2018, 74 (38) : 5408 - 5414
12345