Ring expansion of spirocyclopropanes with stabilized sulfonium ylides: highly diastereoselective synthesis of cyclobutanes

被引：4

作者：

Nambu, Hisanori ^{[1
,2
]}

Onuki, Yuta ^{[1
]}

Aso, Kana ^{[1
]}

Kanamori, Momoka ^{[1
]}

Tomohara, Keisuke ^{[2
]}

Tsuge, Kiyoshi ^{[3
]}

Yakura, Takayuki ^{[1
]}

机构：

[1] Univ Toyama, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

[2] Kyoto Pharmaceut Univ, Lab Pharmaceut Mfg Chem, Kyoto 6078412, Japan

[3] Univ Toyama, Grad Sch Sci & Engn, Gofuku, Toyama 9308555, Japan

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 34期

关键词：

OPENING CYCLIZATION; EFFICIENT SYNTHESIS; CYCLOPROPANE; CYCLOALKANE-1,3-DIONE-2-SPIROCYCLOPROPANES; DERIVATIVES; COMPOUND; STYRENES;

D O I：

10.1039/d3cc06033k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel method was devised for regioselective ring expansion of Meldrum's acid-derived spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones in up to 87% yields without the formation of any isomers. The aforementioned reaction was also applied to the barbituric acid-derived spirocyclopropane, resulting in the formation of the corresponding cyclobutanes. A novel method was devised for regioselective ring expansion of spirocyclopropanes to spirocyclobutanes with stabilized sulfonium ylides, affording 1,2-trans-disubstituted 6,8-dioxaspiro[3.5]nonane-5,9-diones without the formation of any isomers.

引用

页码：4537 / 4540

页数：5

共 50 条

[41] Synthesis of highly stabilized phosphorus ylides from acetylenic esters, CH-acids and triphenylphosphine in aqueous media
Ramazani, A
Dolatyari, L
Kazemizadeh, AR
Ahmadi, E
ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (01) : 297 - 300
[42] Diastereoselective Synthesis of Macrocyclic Spiro and Dispiro-1,4-dithianes,-1,4-oxathianes, and-1,4-dithiepanes through Intramolecular Sulfonium Ylides
Muthusamy, Sengodagounder
Selvaraj, Karuppu
Suresh, Eringathodi
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (01) : 162 - 172
[43] Efficient synthesis of optically active α-quaternary amino acids by highly diastereoselective [2,3]-rearrangement of allylic ammonium ylides
Zhu, Ting-Shun
Xu, Ming-Hua
CHEMICAL COMMUNICATIONS, 2012, 48 (58) : 7274 - 7276
[44] Unified Synthesis of Azepines by Visible-Light-Mediated Dearomative Ring Expansion of Aromatic N-Ylides
Mailloux, Matthew J.
Fleming, Gabrielle S.
Kumta, Shruti S.
Beeler, Aaron B.
ORGANIC LETTERS, 2021, 23 (02) : 525 - 529
[45] Total Synthesis of (±)-Cyclogalgravin and Its Dicarboxyl Analog Using Sc(OTf)3-mediated Highly Diastereoselective Ring Expansion of 1-(Arylhydroxymethyl)cyclopropanecarboxylates
Sakuma, Daichi
Ito, Junki
Sakai, Ryo
Taguchi, Ryota
Nishii, Yoshinori
CHEMISTRY LETTERS, 2014, 43 (05) : 610 - 611
[46] Synthesis of Functionalized Thietanes via Electrophilic Carbenoid-Induced Ring Expansion of Thiiranes with Sulfonium Acylmethylides as Carbene Precursors
Dong, Jun
Du, Hongguang
Xu, Jiaxi
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17): : 10724 - 10739
[47] ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES
ITO, H
MOTOKI, Y
TAGUCHI, T
HANZAWA, Y
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) : 8835 - 8836
[48] Diastereoselective synthesis of functionalized pyrrolidines through N-bromosuccinimide-induced aziridine ring expansion cascade of cinnamylaziridine
Zhou, Jing
Yeung, Ying-Yeung
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (38) : 7482 - 7485
[49] Direct synthesis of pyrrolo[2,1-a]isoquinolines by 1,3-dipolar cycloaddition of stabilized isoquinolinium N-ylides with vinyl sulfonium salts
An, Jing
Yang, Qing-Qing
Wang, Qiang
Xiao, Wen-Jing
TETRAHEDRON LETTERS, 2013, 54 (29) : 3834 - 3837
[50] SYNTHESIS OF HIGHLY STABILIZED YLIDES FROM N-[2-(1,3-BENZAZOLYLMETHYL)]PYRIDINIUM SALTS
CUADRO, AM
NOVELLA, JL
MOLINA, A
ALVAREZBUILLA, J
VAQUERO, JJ
TETRAHEDRON, 1990, 46 (17) : 6033 - 6046

← 1 2 3 4 5 →