Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto N-tert-butanesulfinyl aldimines: synthesis of α-amino ketones

被引：0

作者：

Wang, Cece ^{[1
]}

Zhou, Lu ^{[1
]}

Qiu, Jian ^{[1
]}

Yang, Kai ^{[1
]}

Song, Qiuling ^{[1
,2
]}

机构：

[1] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fujian Prov Univ, Fuzhou 350108, Fujian, Peoples R China

[2] Huaqiao Univ, Inst Next Generat Matter Transformat, Coll Mat Sci Engn, 668 Jimei Blvd, Xiamen 361021, Fujian, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 04期

基金：

中国国家自然科学基金;

关键词：

AZA-BENZOIN REACTIONS; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; RH(I)-CATALYZED ADDITION; EFFICIENT SYNTHESIS; 1,2-AMINO ALCOHOLS; ALDEHYDES; HYDROGENATION; DERIVATIVES; ACCESS;

D O I：

10.1039/d1qo01721g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we present a diastereoselective addition of arylboronic acids to alpha-keto N-tert-butanesulfinyl aldimines catalyzed by a Rh(i) catalyst. This reaction provides a practical method to obtain valuable chiral alpha-amino ketones with excellent diastereoselectivity, featuring operational simplicity, mild reaction conditions and a broad substrate scope.

引用

页码：1016 / 1022

页数：7

共 50 条

[1] Rh-Catalyzed diastereoselective addition of arylboronic acids to α-keto: N-tert -butanesulfinyl aldimines: Synthesis of α-amino ketones
Wang, Cece
Zhou, Lu
Qiu, Jian
Yang, Kai
Song, Qiuling
[J]. Organic Chemistry Frontiers, 2022, 9 (04) : 1016 - 1022
[2] Diastereoselective and enantioselective Rh(l)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines
Weix, DJ
Shi, YL
Ellman, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1092 - 1093
[3] Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines
[J]. 1600, American Chemical Society, Columbus, United States (127):
[4] Stereoselective Coupling of N-tert-Butanesulfinyl Aldimines and β-Keto Acids: Access to β-Amino Ketones
Lahosa, Alejandro
Soler, Tatiana
Arrieta, Ana
Cossio, Fernando P.
Foubelo, Francisco
Yus, Miguel
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14): : 7481 - 7491
[5] Copper-Catalyzed Diastereoselective Addition of Diborylmethane to N-tert-Butanesulfinyl Aldimines: Synthesis of β-Aminoboronates
Park, Jinyoung
Lee, Yeosan
Kim, Junghoon
Cho, Seung Hwan
[J]. ORGANIC LETTERS, 2016, 18 (05) : 1210 - 1213
[6] Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters
Dai, Huixiong
Lu, Xiyan
[J]. ORGANIC LETTERS, 2007, 9 (16) : 3077 - 3080
[7] Asymmetric Synthesis of α-Branched Allylic Amines by the Rh(I)-Catalyzed Addition of Alkenyltrifluoroborates to N-tert-Butanesulfinyl Aldimines
Brak, Katrien
Ellman, Jonathan A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 3850 - +
[8] Asymmetric Rh(I)-Catalyzed Addition of MIDA Boronates to N-tert-Butanesulfinyl Aldimines: Development and Comparison to Trifluoroborates
Brak, Katrien
Ellman, Jonathan A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09): : 3147 - 3150
[9] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Beenen, Melissa A.
Weix, Daniel J.
Ellman, Jonathan A.
[J]. Journal of the American Chemical Society, 2006, 128 (19): : 6304 - 6305
[10] Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Beenen, Melissa A.
Weix, Daniel J.
Ellman, Jonathan A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (19) : 6304 - 6305

← 1 2 3 4 5 →