Chemoselective tandem SN2′/SN2′′/inter- or intramolecular Diels-Alder reaction of γ-vinyl MBH carbonates with phenols and o-hydroxychalcones

被引：5

作者：

Liu, Wei ^{[1
]}

Zhang, Le ^{[1
]}

Liu, Ye ^{[1
]}

Fan, Shi-Lu ^{[1
]}

Dai, Jian-Jun ^{[1
]}

Tao, Wei ^{[1
]}

Zhu, Hui-Xia ^{[1
]}

Xiao, Hua ^{[1
,2
]}

机构：

[1] Hefei Univ Technol, Sch Food & Biol Engn, 485 Danxia Rd, Hefei 230601, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 70期

关键词：

ALLYLIC ALKYLATION; HILLMAN; DIMERIZATION; DERIVATIVES; ANNULATION; ACETATES;

D O I：

10.1039/d2cc03771h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented consecutive S(N)2 '/S(N)2 '' addition of phenol to gamma-vinyl MBH carbonate forms a reactive diene intermediate, followed by a dimerization/elimination process to give functionalized exocyclohexenes with excellent chemoselectivity. When using o-hydroxychalcones as pronucleophiles, an S(N)2 '/S(N)2 ''/intramolecular Diels-Alder reaction sequence occurs, selectively producing a series of pharmaceutically intriguing tricyclic chromane derivatives with good diastereoselectivity. The good nucleophilicity and fair nucleofugicity exhibited by phenoxy anion play a pivotal role in the S(N)2 '' addition step.

引用

页码：9794 / 9797

页数：4

共 50 条

[31] Et2SnCl2 • H2O AND THE TRIGONAL-BIPYRAMIDAL TRANSITION STATE OF A SN2 REACTION
Ye, Fei
Reuter, Hans
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (06) : 1367 - 1369
[32] Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction:: SAR studies on conformationally constrained analogues of Linezolid
Selvakumar, N.
Reddy, B. Yadi
Kumar, G. Sunil
Khera, Manoj Kumar
Srinivas, D.
Kumar, M. Sitararn
Das, Jagattaran
Iqbal, Javed
Trehan, Sanjay
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (16) : 4416 - 4419
[33] PALLADIUM-CATALYZED TANDEM CARBONYLATION AND INTRAMOLECULAR DIELS-ALDER REACTION OF 4-ALKEN-2-YNYL CARBONATES - A NEW SYNTHETIC METHOD FOR POLYCYCLIC COMPOUNDS
MANDAI, T
SUZUKI, S
IKAWA, A
MURAKAMI, T
KAWADA, M
TSUJI, J
TETRAHEDRON LETTERS, 1991, 32 (52) : 7687 - 7688
[34] SYNTHESIS OF BETA-D-MANNOSIDES FROM BETA-D-GLUCOSIDES VIA AN INTRAMOLECULAR SN2 REACTION AT C-2
GUNTHER, W
KUNZ, H
CARBOHYDRATE RESEARCH, 1992, 228 (01) : 217 - 241
[35] Effects of stereochemistry and β-substituents on the rates of vinylic SN2 reaction of hypervalent vinyl(phenyl)-λ3-iodanes with tetrabutylammonium halides
Miyamoto, Kazunori
Okubo, Takuji
Hirobe, Masaya
Kunishima, Munetaka
Ochiai, Masahito
TETRAHEDRON, 2010, 66 (31) : 5819 - 5826
[36] A Highly Convergent Synthesis of Tricyclic N-Heterocycles Coupling an Ugi Reaction with a Tandem SN2′-Heck Double Cyclization
Riva, Renata
Banfi, Luca
Basso, Andrea
Cerulli, Valentina
Guanti, Giuseppe
Pani, Marcella
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5134 - 5143
[37] Intramolecular benzoallene-alkyne cycloaddition initiated by site-selective SN2′ reaction of epoxytetracene en route to π-extended pyracylene
Kitamura, Kei
Asahina, Kenta
Adachi, Kazuhiko
Hamura, Toshiyuki
CHEMICAL COMMUNICATIONS, 2019, 55 (74) : 11021 - 11024
[38] Abnormal eight-membered ring formation through SN2′ intramolecular Nozaki/Kishi reaction in a synthetic approach to a taxane precursor
Muller, B
Férézou, JP
Lallemand, JY
Pancrazi, A
Prunet, J
Prangé, T
TETRAHEDRON LETTERS, 1998, 39 (3-4) : 279 - 282
[39] `Abnormal' eight-membered ring formation through SN2' intramolecular Nozaki/Kishi reaction in a synthetic approach to a taxane precursor
Tetrahedron Lett, 3-4 (279):
[40] COMPETITIVE INTRAMOLECULAR ELECTRON-TRANSFER AND SN2 REACTIONS OF RADICAL-ANIONS - EFFECTS OF SOLVENT POLARITY ON THE REACTION-MECHANISM
KIMURA, N
TAKAMUKU, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (06) : 1668 - 1671

← 1 2 3 4 5 →