Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins DOI Creative Commons
Rahul Sarkar, Sankash Mitra, Santanu Mukherjee

et al.

Chemical Science, Journal Year: 2018, Volume and Issue: 9(26), P. 5767 - 5772

Published: Jan. 1, 2018

The first iridium-catalyzed enantioselective vinylogous allylic alkylation of coumarins is presented. Using easily accessible linear carbonates as the electrophile, this reaction installs unfunctionalized allyl groups at γ-position 4-methylcoumarins in an exclusively branched-selective manner generally high yields with excellent level enantioselectivity (up to 99 : 1 er).

Language: Английский

Palladium‐Catalyzed Asymmetric Allylic Alkylations of Colby Pro‐Enolates with MBH Carbonates: Enantioselective Access to Quaternary C−F Oxindoles DOI
Yi Zhu, Yu Mao, Haibo Mei

et al.

Chemistry - A European Journal, Journal Year: 2018, Volume and Issue: 24(36), P. 8994 - 8998

Published: April 23, 2018

Abstract Owing to the innovative applications of fluorinated compounds in many areas technology and medicine, methods for preparation C−F quaternary fluorine containing are extremely high demand. Here, we report discovery a general procedure an S N 2 reaction catalyzed by Pd/Ding‐SKP‐type ligands, that occurs between Colby pro‐enolates with MBH carbonates afford corresponding products featuring two consecutive stereogenic carbons, including center. The reactions readily occur at ambient temperatures chemical yields excellent chemo‐, diastereo‐ enantioselective manners. This practically attractive stereochemical outcome, coupled operational simplicity structural generality, bodes well synthetic application this process novel class biologically relevant fluorine‐containing compounds.

Language: Английский

Citations

46
SN1-Type Alkylation of N-Heteroaromatics with Alcohols DOI
Mingyan Xiao,

Didi Ren,

Lubin Xu

et al.

Organic Letters, Journal Year: 2017, Volume and Issue: 19(21), P. 5724 - 5727

Published: Oct. 26, 2017

The organocatalytic alkylation of 2-methyl-N-heteroaromatics with alcohols has been achieved via SN1-type C(sp3)–H functionalization, providing a green and efficient synthesis indole ferrocene-functionalized N-heteroaromatics in high yields.

Language: Английский

Citations

40
Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase DOI Creative Commons

Qiupeng Hu,

Azusa Kondoh, Masahiro Terada

et al.

Chemical Science, Journal Year: 2018, Volume and Issue: 9(18), P. 4348 - 4351

Published: Jan. 1, 2018

2-Benzylpyridine N-oxides possessing less acidic α-protons were utilized as pronucleophiles for the first time in enantioselective addition reactions under Brønsted base catalysis.

Language: Английский

Citations

40
Total synthesis of natural productsviairidium catalysis DOI
Changchun Yuan, Bo Liu

Organic Chemistry Frontiers, Journal Year: 2017, Volume and Issue: 5(1), P. 106 - 131

Published: Sept. 18, 2017

An overview of the highlights in total synthesis natural products using iridium as a catalyst is given.

Language: Английский

Citations

39
Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins DOI Creative Commons
Rahul Sarkar, Sankash Mitra, Santanu Mukherjee

et al.

Chemical Science, Journal Year: 2018, Volume and Issue: 9(26), P. 5767 - 5772

Published: Jan. 1, 2018

The first iridium-catalyzed enantioselective vinylogous allylic alkylation of coumarins is presented. Using easily accessible linear carbonates as the electrophile, this reaction installs unfunctionalized allyl groups at γ-position 4-methylcoumarins in an exclusively branched-selective manner generally high yields with excellent level enantioselectivity (up to 99 : 1 er).

Language: Английский

Citations

38