Study of the Halide Salt Catalyzed [3+2] Cycloaddition of a,ß-Epoxy Carboxylate with Isocyanate

被引：2

作者：

Wang Huakun ^{[1
]}

Ren Xiaolong ^{[1
]}

Xuan Yining ^{[1
]}

机构：

[1] Guangdong Pharmaceut Univ, Sch Pharm, Guangzhou 510006, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 44卷 / 01期

关键词：

asymmetric synthesis; 3+2] cycloaddition; oxazolidin-2-one; taxol side chain; ALPHA; BETA-EPOXY ESTERS; CARBON-DIOXIDE; OXAZOLIDINONES; CONVERSION; HETEROCUMULENES; EFFICIENT; EPOXIDES; OXIDE;

D O I：

10.6023/cjoc202305018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3+2] cycloaddition reaction of a,ss-epoxy carboxylate and isocyanate was investigated. By employing magnesium bromide as a catalyst, efficient synthesis of chiral oxazolidin-2-ones was achieved through aforementioned [3+2] cycloaddition reaction. The reaction exhibited good substrate adaptability. For reactions involving chiral epoxide compounds, the product enantiomeric excess remains good. Furthermore, under basic conditions, taxol C-13 side chain ((2R,3S)-methyl 3-benzamido-2-hydroxy-3-phenylpropanoate) was synthesized via ring-opening reaction of the chiral oxazolidin-2-ones product with an optical purity of up to 97% ee.

引用

页码：251 / 258

页数：8

共 28 条

[1] Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters
Afon'kin, A. A.
Kostrikin, L. M.
Shumeiko, A. E.
Popov, A. F.
Matveev, A. A.
Matvienko, V. N.
Zabudkin, A. F.
[J]. RUSSIAN CHEMICAL BULLETIN, 2012, 61 (11) : 2149 - 2162
[2] SYNTHESIS AND REACTIONS OF HETEROCYCLIC METHYL 2-PROPENOATES AND 2,3-EPOXYPROPANOATES WITH NUCLEOPHILES
AGARWAL, KC
KNAUS, EE
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (01) : 65 - 69
[3] STEREOSPECIFIC CYCLOADDITION OF HETEROCUMULENES TO OXIRANES CATALYZED BY ORGANOTIN HALIDE-COMPLEXES
BABA, A
SEKI, K
MATSUDA, H
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (07) : 1925 - 1930
[4] A new semisynthesis of paclitaxel from baccatin III
Baloglu, E
Kingston, DGI
[J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (07): : 1068 - 1071
[5] European perspective and update on the management of complicated skin and soft tissue infections due to methicillin-resistant Staphylococcus aureus after more than 10years of experience with linezolid
Bassetti, M.
Baguneid, M.
Bouza, E.
Dryden, M.
Nathwani, D.
Wilcox, M.
[J]. CLINICAL MICROBIOLOGY AND INFECTION, 2014, 20 : 3 - 18
[6] Fe(II) complexes: reservoirs for Lewis acids and carbenes and their utility in the conversion of CO2 to oxazolidinones
Chen, Fei
Li, Min
Wang, Jingjing
Dai, Bin
Liu, Ning
[J]. JOURNAL OF CO2 UTILIZATION, 2018, 28 : 181 - 188
[7] Oxazolidinones - A review
Diekema, DJ
Jones, RN
[J]. DRUGS, 2000, 59 (01) : 7 - 16
[8] CYCLOADDITION REACTION OF 2,3-DISUBSTITUTED OXIRANES WITH ISOCYANATES BY HIGHLY ACTIVATED CATALYST - PH4SBI-BU3SNI
FUJIWARA, M
BABA, A
TOMOHISA, Y
MATSUDA, H
[J]. CHEMISTRY LETTERS, 1986, (11) : 1963 - 1966
[9] Regioselective syntheses of 3-hydroxy-4-aryl-3,4,5-trihydro-2H-benzo[b][1,4]diazepin-2(1H)-ones and 3-benzylquinoxalin-2(1H)-ones from arylglycidates when exposed to 1,2-diaminobenzenes
Mamedov, Vakhid A.
Mamedova, Vera L.
Syakaev, Victor V.
Voronina, Julia K.
Mahrous, Essam M.
Korshin, Dmitry E.
Latypov, Shamil K.
Sinyashin, Oleg G.
[J]. TETRAHEDRON, 2020, 76 (41)
[10] REACTION OF BENZOYL ISOCYANATE WITH PHOSPHOLENE OXIDE CATALYST
MCGREW, LA
FOLDI, VS
CAMPBELL, TW
SWEENY, W
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) : 3002 - &

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