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

You, Cai1,2; Li, Shuailong1,2; Li, Xiuxiu1,2; Lv, Hui1,2,5; Zhang, Xumu1,2,3,4

2019-09

10.1021/acscatal.9b02667

ACS Catalysis   影响因子和分区

2155-5435

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.

enantioselectivity hydroformylation rhodium lactone lactam

SCI ; EI

英语

通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17213101]

Chemistry

Chemistry, Physical

WOS:000485090400091

AMER CHEMICAL SOC

20193707419473

Amides ; Amines ; Catalysis ; Esters ; Hydroformylation ; Rhodium

Precious Metals:547.1 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Chemical Operations:802.3 ; Organic Compounds:804.1

Web of Science

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

You, Cai,Li, Shuailong,Li, Xiuxiu,et al. Enantioselective Rh-Catalyzed Anti-Markovnikov Hydroformylation of 1,1-Disubstituted Allylic Alcohols and Amines: An Efficient Route to Chiral Lactones and Lactams[J]. ACS Catalysis,2019,9(9):8529-8533.

You, Cai,Li, Shuailong,Li, Xiuxiu,Lv, Hui,&Zhang, Xumu.(2019).Enantioselective Rh-Catalyzed Anti-Markovnikov Hydroformylation of 1,1-Disubstituted Allylic Alcohols and Amines: An Efficient Route to Chiral Lactones and Lactams.ACS Catalysis,9(9),8529-8533.

You, Cai,et al."Enantioselective Rh-Catalyzed Anti-Markovnikov Hydroformylation of 1,1-Disubstituted Allylic Alcohols and Amines: An Efficient Route to Chiral Lactones and Lactams".ACS Catalysis 9.9(2019):8529-8533.