Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes

被引：10

作者：

Kwan, ML ^{[1
]}

Yeung, CW ^{[1
]}

Breno, KL ^{[1
]}

Doxsee, KM ^{[1
]}

机构：

[1] Univ Oregon, Dept Chem, Eugene, OR 97403 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 08期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)02271-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinylsilanes serve as convenient vinyl anion equivalents, but procedures for their stereoselective synthesis from aldehydes are scarce. A variety of aromatic aldehydes are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to the aldehyde followed by treatment with Cp2TiCH2. AlMe2Cl ('Tebbe's reagent'). Halide and alkoxide substituents are tolerated, and (E)-vinylsilanes are formed exclusively in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1411 / 1413

页数：3

共 50 条

[1] A ONE-POT STEREOSELECTIVE SYNTHESIS OF HYDROXY-KETENEDITHIOACETALS FROM ALDEHYDES
TCHERTCHIAN, S
VALLEE, Y
[J]. TETRAHEDRON LETTERS, 1995, 36 (35) : 6225 - 6226
[2] One-Pot Stereoselective Synthesis of (Z)-β-Ketoenamides from β-Halo α, β-Unsaturated Aldehydes
Gogoi, Junali
Gogoi, Pranjal
Boruah, Romesh C.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3483 - 3490
[3] ONE-POT SYNTHESIS OF ALPHA-TRIMETHYLSILYL ENONES FROM VINYLSILANES
ADAM, W
RICHTER, MJ
[J]. SYNTHESIS-STUTTGART, 1994, (02): : 176 - 180
[4] Highly Efficient Microwave-assisted One-Pot Synthesis of Aromatic Nitriles from Aromatic Aldehydes
P. L. Pujari
P. V. Thorat
A. B. Mahipal
R. S. Bhondwe
[J]. Russian Journal of Organic Chemistry, 2019, 55 : 702 - 706
[5] Highly Efficient Microwave-assisted One-Pot Synthesis of Aromatic Nitriles from Aromatic Aldehydes
Pujari, P. L.
Thorat, P. V.
Mahipal, A. B.
Bhondwe, R. S.
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (05) : 702 - 706
[6] A highly stereoselective one-pot asymmetric synthesis of homoallylic amines and amino acids from aldehydes
Loh, TP
Ho, DSC
Xu, KC
Sim, KY
[J]. TETRAHEDRON LETTERS, 1997, 38 (05) : 865 - 868
[7] A one-pot procedure for the synthesis of iodoalkynes from aldehydes
Michel, P
Rassat, A
[J]. TETRAHEDRON LETTERS, 1999, 40 (49) : 8579 - 8581
[8] One-pot synthesis of conjugated alkynenitriles from aldehydes
Kim, Joong-Gon
Lee, Eun Hwa
Jang, Doo Ok
[J]. TETRAHEDRON LETTERS, 2007, 48 (13) : 2299 - 2301
[9] Stereoselective one-pot synthesis of isomaltooligosaccharides
Pastuch, G
Wandzik, I
Szeja, W
[J]. POLISH JOURNAL OF CHEMISTRY, 2003, 77 (08) : 995 - 999
[10] Stereoselective one-pot synthesis of polypropionates
Ho, Guo-Ming
Zulueta, Medel Manuel L.
Hung, Shang-Cheng
[J]. NATURE COMMUNICATIONS, 2017, 8

← 1 2 3 4 5 →