Enantioselective Rh-Catalyzed Anti-Markovnikov Hydroformylation of 1,1-Disubstituted Allylic Alcohols and Amines: An Efficient Route to Chiral Lactones and Lactams

被引：35

作者：

You, Cai ^{[1
,2
]}

Li, Shuailong ^{[1
,2
]}

Li, Xiuxiu ^{[1
,2
]}

Lv, Hui ^{[1
,2
,5
]}

Zhang, Xumu ^{[1
,2
,3
,4
]}

机构：

[1] Wuhan Univ, Minist Educ, Key Lab Biomed Polymers, Wuhan 430072, Hubei, Peoples R China

[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[3] Southern Univ Sci & Technol, Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

[4] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518000, Guangdong, Peoples R China

[5] Wuhan Univ, Coll Chem & Mol Sci, Sauvage Ctr Mol Sci, Engn Res Ctr Organosilicon Cpds & Mat,Minist Educ, Wuhan 430072, Hubei, Peoples R China

来源：

ACS CATALYSIS | 2019年 / 9卷 / 09期

基金：

中国国家自然科学基金;

关键词：

enantioselectivity; hydroformylation; rhodium; lactone; lactam; ASYMMETRIC HYDROFORMYLATION; LIGANDS; DESIGN; ESTERS;

D O I：

10.1021/acscatal.9b02667

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Rh-catalyzed highly enantioselective anti-Markovnikov hydroformylation of 1,1-disubstituted allylic alcohols and amines has been achieved. By using a chiral hybrid phosphorus ligand, a series of challenging 1,1-disubstituted allylic alcohols and amines were transformed to valuable chiral lactones and lactams with good yields and high enantioselectivities (up to 90% yield and 93% enantiomeric excess (ee)) under very mild reaction conditions (50 degrees C, CO/H-2 = 2.5/2.5 bar). Furthermore, gram-scale reaction and diverse synthetic transformations have also been achieved, demonstrating the wide synthetic utility of this methodology.

引用

页码：8529 / 8533

页数：9

共 49 条

[1] Asymmetric Hydroformylation of Z-Enamides and Enol Esters with Rhodium-Bisdiazaphos Catalysts [J].