Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes

被引：6

作者：

Brandt, Agnieszka ^{[1
,2
]}

Wojtasiewicz, Anna ^{[1
]}

Sniezek, Marcin ^{[1
]}

Makosza, Mieczyslaw ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

[2] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

TETRAHEDRON | 2010年 / 66卷 / 18期

关键词：

Carbanions; Aldol reaction; Cyclization; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1016/j.tet.2010.02.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-position of these sulfones on the relative rates of 1,3-intramolecular substitution of the corresponding gamma-chlorocarbanions and their intramolecular addition are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3378 / 3385

页数：8

共 50 条

[31] A FACILE SYNTHESIS OF 3-SUBSTITUTED ISOTHIOCHROMAN
XU, YC
LEBEAU, E
ATTARDO, G
BREINING, T
SYNTHESIS-STUTTGART, 1994, (04): : 363 - 365
[32] 3-SUBSTITUTED THIOPHENES - A STUDY IN SYNTHESIS
GRONOWITZ, S
ARKIV FOR KEMI, 1955, 8 (05): : 441 - 448
[33] The synthesis of 3-substituted derivatives of methylcholanthrene
Fieser, LF
Riegel, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 2561 - 2565
[34] Asymmetric synthesis of 3-substituted γ- and δ-sultams
Enders, D
Moll, A
Bats, JW
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1271 - 1284
[35] A facile synthesis of 3-substituted phthalides
Li, G
Yin, D
Liang, XT
SYNTHETIC COMMUNICATIONS, 2004, 34 (07) : 1183 - 1189
[36] SYNTHESIS OF 3-SUBSTITUTED FARNESYL ANALOGS
GIBBS, RA
KRISHNAN, U
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 203 - MEDI
[37] Synthesis of 3-substituted furans by hydroformylation
Nanayakkara, P
Alper, H
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (4-5) : 545 - 550
[38] SYNTHESIS OF NEW 3-SUBSTITUTED PYRROLES
STEFAN, KP
SCHUHMANN, W
PARLAR, H
KORTE, F
CHEMISCHE BERICHTE, 1989, 122 (01) : 169 - 174
[39] Synthesis of Enantiopure 3-Substituted Morpholines
Bornholdt, Jan
Felding, Jakob
Kristensen, Jesper Langgaard
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7454 - 7457
[40] Synthesis of new 3-substituted aporphines
Berényi, S
Csutorás, C
Gyulai, S
Rusznyák, G
SYNTHETIC COMMUNICATIONS, 2001, 31 (13) : 1987 - 1992

← 1 2 3 4 5 →