A comparison of the benzylic and the allylic group as a donor in the formal [4+2] cycloaddition to tetrahydropyrans using donor-acceptor cyclobutanes

被引：5
作者：
Ahmed, Awais [1 ]
Christie, Steven D. R. [1 ]
Pritchard, Gareth J. [1 ]
机构：
[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 31期
关键词：
Cyclobutanes; Tetrahydropyrans; Cycloaddition; Lewis acids; BIOMIMETIC SYNTHESIS; ALDEHYDES; 3-ETHOXYCYCLOBUTANONES; KETONES; PYRIDOMACROLIDIN; PHENANTHRIDINES; REARRANGEMENT; PALLADIUM; ROUTES;
D O I：
10.1016/j.tetlet.2017.06.046
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The allyl group was shown to be preferred over the benzyl group as a donor in the formal [4+2]-cyclo-addition reaction between a donor-acceptor cyclobutane and various aldehydes to give tetrahydropyrans. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3028 / 3031
页数：4
相关论文
共 35 条
[21]   Formal [4+2] cycloaddition of cyclobutanones bearing alkyne-cobalt complex at their 3-positions [J].
Kawano, Mizuki ;
Kiuchi, Takaaki ;
Matsuo, Jun-ichi ;
Ishibashi, Hiroyuki .
TETRAHEDRON LETTERS, 2012, 53 (04) :432-434
[22]   Enantioselective organocatalytic Michael addition of malonates to α,β-unsaturated aldehydes in water [J].
Ma, Anqi ;
Zhu, Shaolin ;
Ma, Dawei .
TETRAHEDRON LETTERS, 2008, 49 (19) :3075-3077
[23]   BF3•OEt2-Catalyzed Reaction of Donor-Acceptor Cyclobutanes with Terminal Alkynes: Single-Step Access to 2,3-Dihydrooxepines [J].
Machin, Ben P. ;
Pagenkopf, Brian L. .
SYNLETT, 2011, (19) :2799-2802
[24]   Lewis acid-catalyzed intermolecular [4+2] cycloaddition of 3-alkoxycyclobutanones to aldehydes and ketones [J].
Matsuo, Jun-ichi ;
Sasaki, Shun ;
Tanaka, Hiroyuki ;
Ishibashi, Hiroyuki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (35) :11600-+
[25]   A New Synthesis of 2,3-Di- or 2,3,3-Trisubstituted 2,3-Dihydro-4-pyridones by Reaction of 3-Ethoxycyclobutanones and N-p-Toluenesulfonyl Imines Using Titanium(IV) Chloride: Synthesis of (±)-Bremazocine [J].
Matsuo, Jun-ichi ;
Okado, Ryohei ;
Ishibashi, Hiroyuki .
ORGANIC LETTERS, 2010, 12 (14) :3266-3268
[26]   Formal [4+2] cycloaddition between 3-ethoxycyclobutanones and silyl enol ethers [J].
Matsuo, Jun-ichi ;
Negishi, Shoko ;
Ishibashi, Hiroyuki .
TETRAHEDRON LETTERS, 2009, 50 (42) :5831-5833
[27]   Tin(IV) Chloride Catalyzed Cycloaddition Reactions between 3-Ethoxycyclobutanones and Allylsilanes [J].
Matsuo, Jun-ichi ;
Sasaki, Shun ;
Hoshikawa, Takaya ;
Ishibashi, Hiroyuki .
ORGANIC LETTERS, 2009, 11 (17) :3822-3825
[28]   Ytterbium Trif late Catalyzed Synthesis of Alkoxy-Substituted Donor-Acceptor Cyclobutanes and Their Formal [4+2] Cycloaddition with Imines: Stereoselective Synthesis of Piperidines [J].
Moustafa, Mahmoud M. Abd Rabo ;
Pagenkopf, Brian L. .
ORGANIC LETTERS, 2010, 12 (21) :4732-4735
[29]   Formal [4+2] Cycloaddition of Alkoxy-Substituted Donor-Acceptor Cyclobutanes and Aldehydes Catalyzed by Yb(OTf)3 [J].
Moustafa, Mahmoud M. Abd Rabo ;
Stevens, Andrew C. ;
Machin, Ben P. ;
Pagenkopf, Brian L. .
ORGANIC LETTERS, 2010, 12 (21) :4736-4738
[30]   Asymmetric Synthesis of 2,3-Dihydro-4-pyranones by Reaction of Chiral 3-Alkoxycyclobutanone and Aldehydes [J].
Negishi, Shoko ;
Ishibashi, Hiroyuki ;
Matsuo, Jun-ichi .
ORGANIC LETTERS, 2010, 12 (21) :4984-4987
1234