Preparation of Chiral gamma-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes

Yang, Lei1,2,3; Shang, Weidong1; Zhang, Li1; Zhang, Xia1

2022-10-01

10.1021/acs.orglett.2c03090

ORGANIC LETTERS   Impact Factor & Quartile

1523-7060

1523-7052

The first Ni-catalyzed asymmetric reductive coupling of 2-aza-butadiene with aldehydes was achieved to synthesize chiral gamma- secondary amino alcohols. This transformation features good enantioselectivity and tolerance to various functional groups, which may serve as a complementary method to previously reported noble-metal-catalyzed protocols. Through competition reaction, 2-aza-butadiene was proved to be a more reactive coupling component than its full-carbon analogue, 1,3-butadiene. Notably, this reaction delivers beta-siloxyl imine, an aza-aldol-type product which is difficult to access by conventional methods.

SCI

English

NI Journal Papers

Others

[81803359] ; [21907071]

Chemistry

Chemistry, Organic

WOS:000874421300001

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Sichuan Univ, West China Hosp, Inst Resp Hlth, Dept Resp & Crit Care Med,State Key Lab Biotherapy, Chengdu 610041, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518000, Peoples R China

Yang, Lei,Shang, Weidong,Zhang, Li,et al. Preparation of Chiral gamma-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes[J]. ORGANIC LETTERS,2022.

Yang, Lei,Shang, Weidong,Zhang, Li,&Zhang, Xia.(2022).Preparation of Chiral gamma-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes.ORGANIC LETTERS.

Yang, Lei,et al."Preparation of Chiral gamma-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes".ORGANIC LETTERS (2022).