Use of acid fluorides increases the scope of the reductive acylation of esters

被引：21

作者：

Zhang, YD ^{[1
]}

Rovis, T ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 11期

关键词：

D O I：

10.1021/ol049333h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of acyl fluorides in the Rychnovsky reductive acylation of esters allows a variety of esters to be converted to their corresponding alpha-acyloxy ethers in good to excellent yields, without the need to sacrifice an extra equiv of carboxylic acid functionality.

引用

页码：1877 / 1879

页数：3

共 13 条

[1] Peptide synthesis via amino acid halides
Carpino, LA
Beyermann, M
Wenschuh, H
Bienert, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) : 268 - 274
[2] Preparation of acyl fluorides with hydrogen fluoride-pyridine and 1,3-dicyclohexylcarbodiimide
Chen, CP
Chien, CT
Su, CH
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2002, 115 (01) : 75 - 77
[3] General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation
Dahanukar, VH
Rychnovsky, SD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) : 8317 - 8320
[4] Chiral mandelic acid template provides a highly practical solution for (S)-oxybutynin synthesis
Grover, PT
Bhongle, NN
Wald, SA
Senanayake, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) : 6283 - 6287
[5] MOLECULAR-STRUCTURE OF DIMETHYLALUMINUM FLUORIDE TETRAMER, [(CH3)2A1F]4
GUNDERSEN, G
HAUGEN, T
HAALAND, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 54 (JUN16) : 77 - 86
[6] COPPER-ION PROMOTED ESTERIFICATION OF S-2-PYRIDYL THIOATES AND 2-PYRIDYL ESTERS - EFFICIENT METHODS FOR THE PREPARATION OF HINDERED ESTERS
KIM, S
LEE, JI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) : 1712 - 1716
[7] 1ST GENERAL-SYNTHESIS OF MONOSILYL ACETALS - TRIMETHYLSILYL TRAPPING OF THE INTERMEDIATE IN DIBALH REDUCTION OF CARBOXYLIC-ACID ESTERS USING TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
KIYOOKA, S
SHIROUCHI, M
KANEKO, Y
[J]. TETRAHEDRON LETTERS, 1993, 34 (09) : 1491 - 1494
[8] STRUCTURE AND PROPERTIES OF DIETHYLFLUOROALANE (C2H5)2ALF
LAUBENGA.AW
LENGNICK, GF
[J]. INORGANIC CHEMISTRY, 1966, 5 (04) : 503 - &
[9] ORGANIC FLUORINE COMPOUNDS .27. PREPARATION OF ACYL FLUORIDES WITH ANHYDROUS HYDROGEN FLUORIDE - GENERAL USE OF METHOD OF COLSON AND FREDENHAGEN
OLAH, GA
KUHN, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (01) : 237 - &
[10] SYNTHETIC METHODS AND REACTIONS .63. PYRIDINIUM POLY-(HYDROGEN FLUORIDE) (30-PERCENT PYRIDINE 70-PERCENT HYDROGEN-FLUORIDE) - CONVENIENT REAGENT FOR ORGANIC FLUORINATION REACTIONS
OLAH, GA
WELCH, JT
VANKAR, YD
NOJIMA, M
KEREKES, I
OLAH, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) : 3872 - 3881

← 1 2 →