Styrylmalonates as an Alternative to Donor-Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones

被引：29

作者：

Borisov, Denis D. ^{[1
]}

Novikov, Roman A. ^{[1
,2
]}

Eltysheva, Anna S. ^{[1
]}

Tkachev, Yaroslav V. ^{[2
]}

Tomiloy, Yury V. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

[2] Russian Acad Sci, Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

俄罗斯科学基金会;

关键词：

AROMATIC-ALDEHYDES; DERIVATIVES; CYCLOADDITION; NITROSOARENES; CONSTRUCTION; ANNULATION; MECHANISM;

D O I：

10.1021/acs.orglett.7b01556

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for modifying the reactivity of donor-acceptor cyclopropanes (DAC) has been suggested. It involves the use of isomeric styrylmalonates as alternative sources of reactive intermediates. The efficiency of the approach has been demonstrated in reactions with aromatic aldehydes. As a result, a new process for Construction of the 5,6-dihydropyran-2-one skeleton has been developed. It efficiently occurs with high diastereoselectivity in the presence of BF3.Et(2)Q; the products can be easily isolated by crystallization. The subsequent use of the resulting dihydropyranones in syntheses providing convenient access to various classes of compounds with broad molecular diversity has been demonstrated.

引用

页码：3731 / 3734

页数：4

共 50 条

[21] Highly chemo- and enantioselective vinylogous aldol/cyclization cascade reaction to construct chiral 5,6-dihydropyran-2-ones
Zhang, Zhen-Guo
Fu, Jun-Hao
Sha, Feng
Wu, Xin-Yan
TETRAHEDRON, 2018, 74 (27) : 3557 - 3563
[22] Naphthopyranone synthesis via the tandem Michael-Dieckmann reaction of ortho-toluates with 5,6-dihydropyran-2-ones
Tan, Nichole P. H.
Donner, Christopher D.
TETRAHEDRON LETTERS, 2008, 49 (26) : 4160 - 4162
[23] Enantioselective synthesis of mono- and disubstituted 3,6-dihydro-2H-pyrans and 5,6-dihydropyran-2-ones
Izzo, I
Del Gaudio, P
Della Monica, C
Squitieri, M
De Riccardis, F
HETEROCYCLES, 2003, 60 (09) : 2057 - 2063
[24] Computational study on GaCl3-mediated reactions of donor-acceptor cyclopropanes with aromatic aldehydes: mechanism and role of GaCl3 and aldehydes
Tu, Peng-Cheng
Zhou, Lin
Kirillov, Alexander M.
Fang, Ran
Yang, Lizi
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1702 - 1712
[25] A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)cyclodimerization of donor-acceptor cyclopropanes
Ivanova, Olga A.
Budynina, Ekaterina M.
Skvortsov, Dmitriy A.
Limoge, Michelle
Bakin, Andrei V.
Chagarovskiy, Alexey O.
Trushkov, Igor V.
Melnikov, Mikhail Ya
CHEMICAL COMMUNICATIONS, 2013, 49 (98) : 11482 - 11484
[26] Enantioselective (3+2) Annulation of Donor-Acceptor Cyclopropanes with Aldehydes and Ketones Catalyzed by Brønsted Bases
Obregon, Erlaitz B.
Rost, Louise G.
Kocemba, Ida R.
Kristensen, Anne
McLeod, David A.
Jorgensen, Karl Anker
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (42)
[27] Ring expansion of donor-acceptor cyclopropanes bearing arylcarbamoyl group into 1,5-diarylpyrrolidin-2-ones
Vartanova, A. E.
Plodukhin, A. Yu.
Boichenko, M. A.
Shorokhov, V. V.
Zhokhov, S. S.
Trushkov, I. V.
Ivanova, O. A.
RUSSIAN CHEMICAL BULLETIN, 2022, 71 (11) : 2431 - 2440
[28] Fluoroallylboration-Olefination for the Synthesis of (Z)-4,4-Difluoropent-2-enoates and 5,5-Difluoro-5,6-dihydropyran-2-ones
Ramachandran, P. Veeraraghavan
Tafelska-Kaczmarek, Agnieszka
Sakavuyi, Kaumba
Chatterjee, Anamitra
ORGANIC LETTERS, 2011, 13 (06) : 1302 - 1305
[29] Triflic Acid-Catalyzed Cycloisomerization Reactions of Donor-Acceptor Cyclopropanes: Access to Alkyl 5-Arylfuran-2-carboxylates
Zhu, Yuequan
Xu, Panpan
Gong, Yuefa
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11): : 4829 - 4834
[30] Mechanochemistry Enabled Friedel-Crafts Alkylation Reactions of Donor-Acceptor Cyclopropanes with 2-Indolymethanols
Liang, Jinshao
Ruan, Lihong
Shi, Xurong
Chen, Yinzhi
Song, Chuhuang
Xiao, Jun'an
Liu, Zhiping
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (11) : 3437 - 3445

← 1 2 3 4 5 →