Regio- and stereoselective hydrohalogenation of ynamide components in 1,3-butadiynes with in situ generated HX

被引：14

作者：

Ide, Masataka ^{[1
]}

Ohashi, Kazuhiro ^{[1
]}

Mihara, Shigenori ^{[1
]}

Iwasawa, Tetsuo ^{[1
]}

机构：

[1] Ryukoku Univ Otsu, Fac Sci & Technol, Dept Mat Chem, Shiga 5202194, Japan

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 13期

关键词：

Haloenamide; Diene; Hydrohalogenation; Regio- and stereoselective reaction; Enyne; COENZYME-A REDUCTASE; VINYL HALIDES; ALKYNES; ALKENES; ML-236B; I-2; IODOTRIMETHYLSILANE; STEREOCHEMISTRY; HYDROIODINATION; PATHWAYS;

D O I：

10.1016/j.tetlet.2014.02.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple protocol for regio-, and stereoselective hydrohalogenation of ynamide moieties in 1,3-butadiyne structures is described. The facile approach enables exact syn-addition of HX to the diyne components, giving just single isomer of the corresponding dienes and enynes. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2130 / 2133

页数：4

共 62 条

[21] Tacalcitol, an active vitamin D3, induces nerve growth factor production in human epidermal keratinocytes [J].

Fukuoka, M ;

Sakurai, K ;

Ohta, T ;

Kiyoki, M ;

Katayama, I .

SKIN PHARMACOLOGY AND APPLIED SKIN PHYSIOLOGY, 2001, 14 (04) :226-233

[22] Practical procedures for the preparation of N-tert-butyldimethylsilylhydrazones and their use in modified Wolff-Kishner reductions and in the synthesis of vinyl halides and gem-dihalides [J].

Furrow, ME ;

Myers, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5436-5445

[23] Unequivocal SRN1 route of vinyl halides with a multitude of competing pathways:: Reactivity and structure of the vinyl radical intermediate [J].

Galli, C ;

Rappoport, Z .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (08) :580-587

[24] STEREOSELECTIVE AND REGIOSELECTIVE GENERATION OF ALKENYLZINC REAGENTS VIA TITANIUM-CATALYZED HYDROZINCATION OF INTERNAL ACETYLENES [J].

GAO, Y ;

HARADA, K ;

HATA, T ;

URABE, H ;

SATO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) :290-291

[25] ELECTROPHILIC CYCLODIMERIZATIONS OF N-ALKYLACETYLENES WITH HYDROGEN-CHLORIDE [J].

GRIESBAUM, K ;

ELABED, M .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (06) :2001-2008

[26] Chlorides and hydrochlorides from 1-hexyne [J].

Hennion, GF ;

Welsh, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1367-1368

[27] Long-term clinical effects of epalrestat, an aldose reductase inhibitor, on progression of diabetic neuropathy and other microvascular complications: multivariate epidemiological analysis based on patient background factors and severity of diabetic neuropathy [J].

Hotta, N. ;

Kawamori, R. ;

Fukuda, M. ;

Shigeta, Y. .

DIABETIC MEDICINE, 2012, 29 (12) :1529-1533

[28] STEREOCHEMISTRY OF THE WURTZ-FITTIG PREPARATION OF VINYLSILANES [J].

HUDRLIK, PF ;

KULKARNI, AK ;

JAIN, S ;

HUDRLIK, AM .

TETRAHEDRON, 1983, 39 (06) :877-882

[29]

KAMIYA N, 1990, SYNLETT, P675

[30] Highly Selective Hydroiodation of Alkynes Using an Iodine-Hydrophosphine Binary System [J].

Kawaguchi, Shin-ichi ;

Ogawa, Akiya .

ORGANIC LETTERS, 2010, 12 (09) :1893-1895

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