A novel route to fully substituted cyanoallenes from three components, ketones, chloromethyl p-tolyl sulfoxide, and nitriles, via α-bromocyclopropyl p-tolyl sulfoxides

被引：12

作者：

Satoh, T ^{[1
]}

Gouda, Y ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

allene; cyanoallene; sulfoxide; sulfoxide-lithium exchanged; lithium cyclopropylidene;

D O I：

10.1016/j.tetlet.2006.01.161

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-chlorovinyl p-tolyl sulfoxides. which were derived front ketones and chloromethyl p-tolyl sulfoxide in high yields, with lithium alpha-carbanion of nitriles gave the adducts in quantitative yields. The adducts were converted to alpha-bromocyclopropyl p-tolyl sulfoxides in two steps in good yields. Finally, the sulfoxides were treated with excess lithium carbanion of isobutyronitrile to afford fully Substituted cyanoallenes in high to quantitative yields via sulfoxide-lithium exchange reaction. This procedure offers a novel synthetic method for fully substituted cyanoallenes with coupling of three components (ketones, chloromethyl p-tolyl sulfoxide, and nitriles) in good overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2835 / 2838

页数：4

共 45 条

[1] A synthesis, including asymmetric synthesis, of α-quaternary α-amino aldehydes from ketones and chloromethyl p-tolyl sulfoxide via sulfinylaziridines
Satoh, Tsuyoshi
Endo, Juri
Ota, Hiroyuki
Chyouma, Toshio
TETRAHEDRON, 2007, 63 (22) : 4806 - 4813
[2] A synthesis of optically active α-quaternary α-amino acids and esters by assembling three components, ketones, (R)-chloromethyl p-tolyl sulfoxide, and sodium azide, via sulfinyloxiranes
Satoh, Tsuyoshi
Hirano, Mizue
Kuroiwa, Akio
Kaneko, Youhei
TETRAHEDRON, 2006, 62 (39) : 9268 - 9279
[3] A new and general synthesis of chiral β-ketosulfoxides by reaction of (+)-(R)-methyl p-tolyl sulfoxide with nitriles
Vleggaar, R
Zeevaart, JG
TETRAHEDRON LETTERS, 1999, 40 (52) : 9301 - 9303
[4] Synthesis of conjugated enynes by assembly of three components, ketones, chloromethyl p-tolyl sulfoxide, and acetylenes, with the magnesium carbenoid 1,2-CC insertion as the key reaction
Saitoh, Hideki
Ishida, Naoyuki
Satoh, Tsuyoshi
TETRAHEDRON LETTERS, 2010, 51 (04) : 633 - 637
[5] Efficient synthesis of chrysanthemate precursor from chiral p-tolyl β-(trimethylsilyl)ethyl sulfoxide
Nakamura, S
Watanabe, Y
Toru, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23): : 3403 - 3404
[6] A short and stereoselective synthesis of highly substituted cyclopropanes from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide
Miyagawa, Toshifumi
Tatenuma, Toshinori
Tadokoro, Makoto
Satoh, Tsuyoshi
TETRAHEDRON, 2008, 64 (22) : 5279 - 5284
[7] A new synthesis, including asymmetric synthesis, of spiro[4.n]alkenones from three components:: cyclic ketones, chloromethyl p-tolyl sulfoxide, and acetonitrile;: and a formal total synthesis of racemic acorone
Satoh, T
Kawashima, T
Takahashi, S
Sakai, K
TETRAHEDRON, 2003, 59 (48) : 9599 - 9607
[8] A short synthesis of α-allenic alcohols from α,β-unsaturated carbonyl compounds with dichloromethyl p-tolyl sulfoxide
Satoh, Tsuyoshi
Noguchi, Takafumi
Miyagawa, Toshifumi
TETRAHEDRON LETTERS, 2008, 49 (39) : 5689 - 5692
[9] Syntheses and luminescence properties of two novel lanthanide (III) perchlorate complexes with phenacyl p-tolyl sulfoxide
Feng, Shu-Yan
Li, Wen-Xian
Zheng, Yu-Shan
Xin, Xiao-Dong
Guo, Feng
Cao, Xiao-Fang
JOURNAL OF LUMINESCENCE, 2015, 162 : 92 - 96
[10] (Diphenoxyphosphoryl)methyl p-tolyl sulfoxide: A new reagent for Z-selective synthesis of racemic and optically active vinyl sulfoxides
Midura, Wanda H.
Ewas, Ashraf M. Mohamed
Mikolajczyk, Marian
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (03) : 535 - 540

← 1 2 3 4 5 →