Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline

被引：14

作者：

Ait-Youcef, Ramzi ^{[1
]}

Kalch, Delphine ^{[1
]}

Moreau, Xavier ^{[1
]}

Thomassigny, Christine ^{[1
]}

Greck, Christine ^{[1
]}

机构：

[1] Univ Versailles St Quentin En Yvelines, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 05期

关键词：

Electrophilic amination; organocatalysis; tert-butoxyproline; azodicarboxylate; alpha-hydrazinoalcohol; ELECTROPHILIC AMINATION; CARBONYL-COMPOUNDS; ORGANOCATALYSIS; ACID; CARBANIONS;

D O I：

10.2174/157017809788681293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric electrophilic alpha-amination of aldehydes and ketones is described using trans-3-tert-butoxy-L-proline and trans-4-tert-butoxy-L-proline as efficient catalysts. Good yields and high enantioselectivities are obtained working at 0 degrees C or at room temperature with a catalyst loading of only 5 mol%.

引用

页码：377 / 380

页数：4

共 50 条

[41] Selective synthesis of secondary amines by Pt nanowire catalyzed reductive amination of aldehydes and ketones with ammonia
Qi, Fenqiang
Hu, Lei
Lu, Shuanglong
Cao, Xueqin
Gu, Hongwei
CHEMICAL COMMUNICATIONS, 2012, 48 (77) : 9631 - 9633
[42] ASYMMETRIC TRIFLUOROMETHYLATION OF ALDEHYDES AND KETONES WITH TRIFLUOROMETHYLTRIMETHYSILANE CATALYZED BY CHIRAL QUATERNARY AMMONIUM FLUORIDES
ISEKI, K
NAGAI, T
KOBAYASHI, Y
TETRAHEDRON LETTERS, 1994, 35 (19) : 3137 - 3138
[43] Ir/XuPhos-catalyzed direct asymmetric reductive amination of ketones with secondary amines
Luo, Zhou
Fan, Tianxiang
Luo, Jingyan
Liu, Yuanyuan
Zhang, Junliang
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (23): : 6735 - 6741
[44] Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones
Zhu, Dong-Xing
Xu, Ming-Hua
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (02) : 255 - 275
[45] L-proline-catalyzed Michael addition of aldehydes and unmodified ketones to nitro olefins accelerated by Et3N
Choudary, B. M.
Rajasekhar, Ch. V.
Krishna, G. Gopi
Reddy, K. Rajender
SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 91 - 98
[46] Organocatalytic asymmetric synthesis of (-)-δ-coniceine based on sequential proline-catalyzed asymmetric α-amination-HWE olefination
Panchgalle, Sharad P.
Bidwai, Harshad B.
Chavan, Subhash P.
Kalkote, Uttam R.
TETRAHEDRON-ASYMMETRY, 2010, 21 (19) : 2399 - 2401
[47] Proline catalyzed sequential α-amination/Prins/Ritter amidation of aldehydes: new method of construction of tetrahydropyran units
Ahuja, Brijbhushan
Gadakh, Sunita
Sudalai, Arumugam
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2019, 58 (09): : 1019 - 1028
[48] Transformations and Tautomeric Equilibrium among Different Intermediates in Proline-Catalyzed Reactions of Aldehydes or Ketones
Gan, Li-hua
Chang, Qing
Zhou, Jin
CHINESE JOURNAL OF CHEMICAL PHYSICS, 2013, 26 (01) : 54 - 60
[49] Diastereoselective aldol reaction of N,N-dibenzyl-α-arnino aldehydes with ketones catalyzed by proline
Pan, QB
Zou, BL
Wang, YJ
Ma, DW
ORGANIC LETTERS, 2004, 6 (06) : 1009 - 1012
[50] Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline
Iseki, K
Kuroki, Y
Takahashi, M
Kishimoto, S
Kobayashi, Y
TETRAHEDRON, 1997, 53 (10) : 3513 - 3526

← 1 2 3 4 5 →