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
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
[1]   Practical routes to diacetylenic ketones and their application for the preparation of alkynyl substituted pyridines, pyrimidines and pyrazoles [J].
Adamo, MFA ;
Adlington, RM ;
Baldwin, JE ;
Pritchard, GJ ;
Rathmell, RE .
TETRAHEDRON, 2003, 59 (13) :2197-2205
[2]   Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide [J].
Adlington, RM ;
Baldwin, JE ;
Mayweg, AVW ;
Pritchard, GJ .
ORGANIC LETTERS, 2002, 4 (17) :3009-3011
[3]   A versatile approach to pyrimidin-4-yl substituted alpha-amino acids from alkynyl ketones; the total synthesis of L-lathyrine [J].
Adlington, RM ;
Baldwin, JE ;
Catterick, D ;
Pritchard, GJ .
CHEMICAL COMMUNICATIONS, 1997, (18) :1757-1758
[4]   A biomimetic synthesis of lucidene [J].
Adlington, RM ;
Baldwin, JE ;
Pritchard, GJ ;
Williams, AJ ;
Watkin, DJ .
ORGANIC LETTERS, 1999, 1 (12) :1937-1939
[5]   A mild Lewis acid mediated epoxy-ester to bicyclic ortho ester rearrangement [J].
Ahmed, Awais ;
Christie, Steven D. R. ;
Elsegood, Mark R. J. ;
Pritchard, Gareth J. .
CHEMICAL COMMUNICATIONS, 2013, 49 (68) :7489-7491
[6]   Novel C-4 heteroaromatic kainoid analogues: A parallel synthesis approach [J].
Baldwin, JE ;
Fryer, AM ;
Pritchard, GJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (03) :309-311
[7]   Total synthesis of pyridovericin: Studies toward the biomimetic synthesis of pyridomacrolidin [J].
Baldwin, JE ;
Adlington, RM ;
Conte, A ;
Irlapati, NR ;
Marquez, R ;
Pritchard, GJ .
ORGANIC LETTERS, 2002, 4 (13) :2125-2127
[8]   Synthetic and mechanistic studies of the retro-Claisen rearrangement .3. A route to enantiomerically pure vinyl cyclobutane diesters via a highly diastereoselective syn S(N)2' reaction and their rearrangement to enantiomerically pure dihydrooxacenes [J].
Boeckman, RK ;
Reeder, MR .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (19) :6456-6457
[9]   Palladium-mediated synthesis of phenanthridines: The first report of palladium insertion into imidoyl selenides [J].
Bowman, W. Russell ;
Lyon, Jessica E. ;
Pritchard, Gareth J. .
SYNLETT, 2008, (14) :2169-2171
[10]   Palladium and radical routes to phenanthridines [J].
Bowman, W. Russell ;
Lyon, Jessica E. ;
Pritchard, Gareth J. .
ARKIVOC, 2012, :210-227