Multiple Activation Catalyst for Asymmetric [4+2] Cycloaddition of Aldehydes with Dienes

被引：0

作者：

Tomifuji, Rei ^{[1
]}

Murano, Shunpei ^{[1
]}

Teranishi, Satoru ^{[1
]}

Kuroda, Daiki ^{[1
]}

Kurahashr, Takuya ^{[1
]}

Matsubara, Seijiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Mat Chem, Nishikyo Ku, Kyoto 6158510, Japan

来源：

SYNLETT | 2021年 / 32卷 / 19期

关键词：

operando XAFS; DFT; iron; asymmetric cycloaddition; Diels-Alder; DIELS-ALDER REACTION; CHIRAL PHOSPHORIC-ACID; LEWIS-ACID; CARBONYL-COMPOUNDS; IRON; POLYMERIZATION; ION;

D O I：

10.1055/s-0040-1720885

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective oxa-Diels-Alder reaction of nonactivated substrates by utilizing FeCl3 and a 1,1'-bi-2-naphthol (BINOL) derived chiral phosphoric acid as a multiple activation catalyst is reported. Various oxygen-containing six-membered heterocycles were obtained in high yields and in an enantioselective manner. Density functional theory (DFT) calculations elucidate that both Lewis acidic and Bronsted acidic moieties in the catalyst system synergistically activate two lone pairs of an aldehyde to facilitate enantioselective addition reaction of dienes.

引用

页码：1943 / 1947

页数：5

共 44 条

[11] Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid:: Application to catalytic asymmetric allylation of aldehydes [J].

Hanawa, H ;

Hashimoto, T ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1708-1709

[12] Double coordination and activation ability of methylalumoxane (MAO) for hetero functionality: Pivotal role as polymerization cocatalyst [J].

Hanawa, H ;

Abe, N ;

Maruoka, K .

TETRAHEDRON LETTERS, 1999, 40 (29) :5365-5368

[13] Boron Tribromide-Assisted Chiral Phosphoric Acid Catalyst for a Highly Enantioselective Diels-Alder Reaction of 1,2-Dihydropyridines [J].

Hatano, Manabu ;

Goto, Yuta ;

Izumiseki, Atsuto ;

Akakura, Matsujiro ;

Ishihara, Kazuaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (42) :13472-13475

[14] Initiators for Radical Cation-induced [2+2]- and [4+2]-Cycloadditions of Electron-rich Alkenes [J].

Horibe, Takahiro ;

Ishihara, Kazuaki .

CHEMISTRY LETTERS, 2020, 49 (01) :107-113

[15] Structure and Reactivity of Aromatic Radical Cations Generated by FeCl3 [J].

Horibe, Takahiro ;

Ohmura, Shuhei ;

Ishihara, Kazuaki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (05) :1877-1881

[16] Revealing Noncovalent Interactions [J].

Johnson, Erin R. ;

Keinan, Shahar ;

Mori-Sanchez, Paula ;

Contreras-Garcia, Julia ;

Cohen, Aron J. ;

Yang, Weitao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (18) :6498-6506

[17]

Jorgensen KA, 2000, ANGEW CHEM INT EDIT, V39, P3558, DOI 10.1002/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO

[18]

2-I

[19] Catalytic asymmetric methallylation and propargylation of aldehydes with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide [J].

Konishi, S ;

Hanawa, H ;

Maruoka, K .

TETRAHEDRON-ASYMMETRY, 2003, 14 (12) :1603-1605

[20] Iron Corrole-catalyzed [4+2] Cycloaddition of Dienes and Aldehydes [J].

Kuwano, Toru ;

Kurahashi, Takuya ;

Matsubara, Seijiro .

CHEMISTRY LETTERS, 2013, 42 (10) :1241-1243

← 1 2 3 4 5 →