One-Pot Aminoalkylation of Aldehydes: Diastereoselective Synthesis of Vicinal Diamines with Azaarylmethylamines

被引：8

作者：

Guan, Haixing ^{[1
]}

Cao, Xianzhong ^{[1
]}

Walsh, Patrick J. ^{[2
]}

Mao, Jianyou ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Inst Adv Synth, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China

[2] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 21期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

STEREOSELECTIVE-SYNTHESIS; MANNICH REACTION; STEREOCONTROLLED SYNTHESIS; ORGANOMETALLIC REAGENTS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; AMINATIVE UMPOLUNG; LITHIUM AMIDES; ALPHA; IMINES;

D O I：

10.1021/acs.orglett.9b03287

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of vicinal diamines with azaarylmethylamines and aldehydes is reported. A diverse array of vicinal diamines could be achieved in up to 92% yield with good to excellent diastereoselectivities (up to 20:1). The tandem reaction takes place under mild conditions and provides an alternative strategy for the synthesis of vicinal diamines.

引用

页码：8679 / 8683

页数：5

共 50 条

[21] Synthesis of Primary Amines by One-Pot Reductive Amination of Aldehydes
Ayedi, Mohamed Ali
Le Bigot, Yves
Ammar, Houcine
Abid, Souhir
El Gharbi, Rachid
Delmas, Michel
SYNTHETIC COMMUNICATIONS, 2013, 43 (16) : 2127 - 2133
[22] One-pot synthesis of oxazolines and application to the cyanosilylation of prochiral aldehydes
M. Luo
B. Yan
Research on Chemical Intermediates, 2015, 41 : 1171 - 1180
[23] One-Pot Synthesis of Hydroxamic Acids from Aldehydes and Hydroxylamine
Dettori, Giovanna
Gaspa, Silvia
Porcheddu, Andrea
De Luca, Lidia
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) : 2709 - 2713
[24] One-pot synthesis of epoxides from benzyl alcohols and aldehydes
Alfonzo, Edwin
Mendoza, Jesse W. L.
Beeler, Aaron B.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2308 - 2312
[25] An effective one-pot synthesis of aldehydes from acid chlorides
Choi, Seong Jib
Do Lee, Sang
An, Duk Kenn
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (08): : 1449 - 1450
[26] An improved one-pot procedure for the synthesis of alkynes from aldehydes
Muller, S
Liepold, B
Roth, GJ
Bestmann, HJ
SYNLETT, 1996, (06) : 521 - &
[27] Automated One-pot Library Synthesis with Aldehydes as Radical Precursors
Ruiz, Adrian Luguera
Pijper, Brenda
Linares, Maria Lourdes
Canellas, Santiago
Protti, Stefano
Fagnoni, Maurizio
Alcazar, Jesus
CHEMISTRY-METHODS, 2025, 5 (02):
[28] A one-pot procedure for the synthesis of alkynes and bromoalkynes from aldehydes
Michel, P
Gennet, D
Rassat, A
TETRAHEDRON LETTERS, 1999, 40 (49) : 8575 - 8578
[29] Photoorganocatalytic One-Pot Synthesis of Hydroxamic Acids from Aldehydes
Papadopoulos, Giorgos N.
Kokotos, Christoforos G.
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6964 - 6967
[30] One-Pot Synthesis of Isoxazolines from Aldehydes Catalyzed by Iodobenzene
Han, Liuquan
Zhang, Bijun
Xiang, Changbin
Yan, Jie
SYNTHESIS-STUTTGART, 2014, 46 (04): : 503 - 509

← 1 2 3 4 5 →