Efficient diastereo- and enantioselective synthesis of α,β-disubstituted γ-phosphono sulfonates

被引：9

作者：

Enders, Dieter ^{[1
]}

Mirjafary, Zohreh ^{[1
,2
]}

Saeidian, Hamdollah ^{[1
,2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

[2] Sharif Univ Technol, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 21期

关键词：

ORGANOCATALYTIC CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; MICHAEL ADDITION; DERIVATIVES; INHIBITORS; ALDEHYDES; NITRO; ACIDS;

D O I：

10.1016/j.tetasy.2009.10.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first asymmetric synthesis of alpha,beta-disubstituted gamma-phosphono sulfonates is reported. The key step is the Michael addition of a lithiated enantiopure sulfonate bearing an inexpensive chiral sugar auxiliary to alpha,beta-unsaturated phosphonates in good diastereoselectivities. After chromatographic purification, the cleavage of the chiral sugar auxiliary proceeds without any epimerization or racemization to form the corresponding isopropyl sulfonate in very good overall yield (75%) and excellent diastereomeric and enantiomeric excess (de, ee >= 95%). (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2429 / 2431

页数：3

共 50 条

[31] Diastereo- and Enantioselective Direct Aldol Reactions in Aqueous Medium: A New Highly Efficient Proline-Sugar Chimeric Catalyst
Pedatella, Silvana
De Nisco, Mauro
Mastroianni, Domenico
Naviglio, Daniele
Nucci, Ada
Caputo, Romualdo
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1443 - 1446
[32] Substituted Imidazoline Synthesis: A Diastereo- and Enantioselective aza-Henry Route to a Human Proteasome Modulator
Sprague, Daniel J.
Johnston, Jeffrey N.
ORGANIC LETTERS, 2020, 22 (21) : 8496 - 8499
[33] Diastereo- and Enantioselective Synthesis of Hexasubstituted Cyclohexanes via a Metal-Organocatalytic Quadruple Cascade Sequence
Lee, Hwa-Jung
Shyam, Pranab Kumar
Yoon, Woojin
Yun, Hoseop
Jang, Hye-Young
SYNTHESIS-STUTTGART, 2014, 46 (10): : 1329 - 1333
[34] Bronsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams
Chen, Peng-Fei
Zhou, Bo
Wu, Peng
Wang, Binju
Ye, Long-Wu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) : 27164 - 27170
[35] Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot
Jiang, Yan
Deiana, Luca
Alimohammadzadeh, Rana
Liu, Leifeng
Sun, Junliang
Cordova, Armando
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (09) : 1158 - 1164
[36] Diastereo- and Enantioselective Synthesis of Quaternary α-Amino Acid Precursors by Copper -Catalyzed Propargylation
Zhu, Qiongqiong
Meng, Beibei
Gu, Congzheng
Xu, Ye
Chen, Jie
Lei, Chuanhu
Wu, Xiaoyu
ORGANIC LETTERS, 2019, 21 (24) : 9985 - 9989
[37] Highly diastereo- and enantioselective synthesis of protected anti-1,3-diols
Enders, D
Hundertmark, T
Lampe, C
Jegelka, U
Scharfbillig, I
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (12) : 2839 - 2849
[38] Highly diastereo- and enantioselective direct aldol reactions in water
Hayashi, Y
Sumiya, T
Takahashi, J
Gotoh, H
Urushima, T
Shoji, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) : 958 - 961
[39] Catalytic Diastereo- and Enantioselective Synthesis of TertiaryTrifluoromethyl Carbinols through a Vinylogous Aldol Reaction ofAlkylidenepyrazolones with Trifluoromethyl Ketones
Carceller-Ferrer, Laura
Gonzalez del Campo, Aleix
Vila, Carlos
Blay, Gonzalo
Carmen Munoz, M.
Pedro, Jose R.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07) : 4538 - 4549
[40] Picolylamine as an organocatalyst template for highly diastereo- and enantioselective aqueous aldol reactions
Nugent, Thomas C.
Umar, M. Naveed
Bibi, Ahtaram
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (18) : 4085 - 4089

← 1 2 3 4 5 →