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

[41] Diastereo- and enantioselective synthesis of syn-2,3-disubstituted 1,4-diketones via oxidative coupling of metalated hydrazones
Enders, D
Muller, P
Klein, D
SYNLETT, 1998, (01) : 43 - +
[42] Copper-Catalyzed Diastereo- and Enantioselective Borylative Cyclization
Manna, Srimanta
CATALYSTS, 2022, 12 (07)
[43] Diastereo- and Enantioselective Synthesis of Spirooxindoles with Contiguous Tetrasubstituted Stereocenters via Catalytic Coupling of Two Tertiary Radicals
Song, Zhi-Yong
Chen, Kun-Quan
Chen, Xiang-Yu
Ye, Song
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (05) : 2966 - 2970
[44] Diastereo- and Enantioselective Synthesis of Spiro-Pyrrolidine-Pyrazolones by Squaramide-Catalyzed Cascade Aza-Michael/Michael Reactions
Li, Jun-Hua
Wen, Hongliang
Liu, Lei
Du, Da-Ming
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2492 - 2499
[45] Highly Diastereo- and Enantioselective Synthesis of Spiro-tetrahydrofuran-pyrazolones via Organocatalytic Cascade Reaction between γ-Hydroxyenones and Unsaturated Pyrazolones
Mondal, Buddhadeb
Maity, Rajendra
Pan, Subhas Chandra
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (15) : 8645 - 8654
[46] Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers
Page, Abigail
Clayden, Jonathan
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1327 - 1333
[47] An Engineered Imine Reductase for Highly Diastereo- and Enantioselective Synthesis of β-Branched Amines with Contiguous Stereocenters
Zhu, Zhen-Yu
Shi, Min
Li, Chen-Lin
Gao, Yun-Fei
Shen, Xin-Yuan
Ding, Xu-Wei
Chen, Fei-Fei
Xu, Jian-He
Chen, Qi
Zheng, Gao-Wei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (47)
[48] Diastereo- and enantioselective synthesis of 1,2,3-substituted cyclopropanes with zinc carbenoids
Charette, AB
Lemay, J
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (10): : 1090 - 1092
[49] Asymmetric Total Synthesis of (-)-Englerin A through Catalytic Diastereo- and Enantioselective Carbonyl Ylide Cycloaddition
Hanari, Taiki
Shimada, Naoyuki
Kurosaki, Yasunobu
Thrimurtulu, Neetipalli
Nambu, Hisanori
Anada, Masahiro
Hashimoto, Shunichi
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (33) : 11671 - 11676
[50] Cu-Catalyzed Diastereo- and Enantioselective Synthesis of Borylated Cyclopropanes with Three Contiguous Stereocenters
Gao, Chao
Tang, Kai
Yang, Xi
Gao, Shen
Zheng, Qingshu
Chen, Xiangyang
Liu, Jiawang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (04) : 3360 - 3370

← 1 2 3 4 5 →