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

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