Effect of achiral and mixed chiral ligands on the asymmetric synthesis of γ-nitrophosphonates via Michael addition

被引：12

作者：

Rai, Vishal ^{[1
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 07期

关键词：

D O I：

10.1016/j.tetasy.2008.03.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Changes in the diastereo- and/or enantioselectivity were observed when the Li-cinchonine catalyzed conjugate addition of phosphonates to nitroalkenes was carried out in the presence of achiral/chiral additives. Although the conjugate addition in the absence of such additives proceeded in better yields and selectivities as reported previously, the dramatic change in selectivity in the presence of additives provides an opportunity to synthesize different stereoisomers of the product, gamma-nitrophosphonate, using primarily the same chiral source. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：767 / 772

页数：6

共 50 条

[21] Self-assembly of achiral and chiral macrocyclic ligands: synthesis, protonation constants, conformation and asymmetric catalysis
Gao, J
Martell, AE
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (15) : 2795 - 2800
[22] Chiral ionic Bronsted acid-achiral Bronsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins
Uraguchi, Daisuke
Kinoshita, Natsuko
Nakashima, Daisuke
Ooi, Takashi
CHEMICAL SCIENCE, 2012, 3 (11) : 3161 - 3164
[23] Asymmetric Synthesis of an Amino Acid Derivative from Achiral Aroyl Acrylamide by Reversible Michael Addition and Preferential Crystallization
Kaji, Yuki
Uemura, Naohiro
Kasashima, Yoshio
Ishikawa, Hiroki
Yoshida, Yasushi
Mino, Takashi
Sakamoto, Masami
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (46) : 16429 - 16432
[24] Synthesis of the atropurpuran A-ring via an organocatalytic asymmetric intramolecular Michael addition
Chen, Huan
Zhang, Dan
Xue, Fei
Qin, Yong
TETRAHEDRON, 2013, 69 (15) : 3141 - 3148
[25] Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study
Mkrtchyan, Anna F.
Tovmasyan, Anna S.
Paloyan, Ani M.
Sargsyan, Armen S.
Simonyan, Hayarpi M.
Sahakyan, Lusine Yu
Petrosyan, Satenik Gh
Hayriyan, Liana A.
Sargsyan, Tatev H.
SYNLETT, 2022, 33 (20) : 2013 - 2018
[26] Asymmetric synthesis of β-amino-cyclohexyl sulfonates via aza Michael addition
Enders, D
Wallert, S
SYNLETT, 2002, (02) : 304 - 306
[27] STEREOSELECTIVE SYNTHESIS OF MELATONIN RECEPTOR AGONIST RAMELTEON VIA ASYMMETRIC MICHAEL ADDITION
Zhang, Xuan
Yuan, Wei
Luo, Yu
Huang, Qing-Qing
Lu, Wei
HETEROCYCLES, 2012, 85 (01) : 73 - 84
[28] Asymmetric synthesis of α-substituted β-formyl δ-lactones via a Michael addition/α-alkylation protocol
Enders, D
Vázquez, J
SYNLETT, 1999, (05) : 629 - 631
[29] Asymmetric synthesis of chiral α-keto esters via Grignard addition to oxalates
MaGee, DI
Mallais, TC
Eic, M
TETRAHEDRON-ASYMMETRY, 2003, 14 (20) : 3177 - 3181
[30] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine
Andrey, O
Alexakis, A
Bernardinelli, G
ORGANIC LETTERS, 2003, 5 (14) : 2559 - 2561

← 1 2 3 4 5 →