Regioselective reductive coupling of alkynes and aldehydes leading to allylic alcohols

被引：71

作者：

Takai, K ^{[1
]}

Sakamoto, S ^{[1
]}

Isshiki, T ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 05期

关键词：

D O I：

10.1021/ol0272996

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of a mixture of a terminal alkyne and an aldehyde with CrCl2 and a catalytic amount of NICl2 and triphenylphosphine in the presence of water in DMF at 25 degreesC gives a 1,2-disubstituted allylic alcohol regioselectively.

引用

页码：653 / 655

页数：3

共 22 条

[1] Preparation and reactivity of nickel(0) complexes with η2-coordinated alkynylphosphines [J].

Bennett, MA ;

Castro, J ;

Edwards, AJ ;

Kopp, MR ;

Wenger, E ;

Willis, AC .

ORGANOMETALLICS, 2001, 20 (05) :980-989

[2] A NOVEL METHOD FOR SYNTHESIS OF BOTH CIS- AND TRANS-VINYL BROMIDES FROM 1-ALKYNES VIA HYDROBORATION [J].

BROWN, HC ;

BOWMAN, DH ;

MISUMI, S ;

UNNI, MK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4531-&

[3] CHEMISTRY OF ORGANOCHROMIUM(III) COMPLEXES [J].

ESPENSON, JH .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (05) :222-227

[4] REDUCTION OF ORGANIC COMPOUNDS WITH CHROMIUM(2) SALTS [J].

HANSON, JR ;

PREMUZIC, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (04) :247-&

[5] CHROMIUM(II)-MEDIATED NICKEL(II)-CATALYZED CYCLIZATIONS OF (IODOARYL)-SUBSTITUTED ALKYNES AND ALKYNALS [J].

HODGSON, DM ;

WELLS, C .

TETRAHEDRON LETTERS, 1994, 35 (10) :1601-1604

[6] Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes [J].

Huang, WS ;

Chan, J ;

Jamison, TF .

ORGANIC LETTERS, 2000, 2 (26) :4221-4223

[7] CATALYTIC EFFECT OF NICKEL(II) CHLORIDE AND PALLADIUM(II) ACETATE ON CHROMIUM(II)-MEDIATED COUPLING REACTION OF IODO OLEFINS WITH ALDEHYDES [J].

JIN, H ;

UENISHI, J ;

CHRIST, WJ ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5644-5646

[8]

KAMIYA N, 1990, SYNLETT, P675

[9] TRANSITION-METAL ACTIVATED ORGANIC-COMPOUNDS .17. SURPRISING STABILITY OF NUCLEOPHILIC CRIII-ALKYLATING AND CRIII-ALLYLATING REAGENTS TOWARDS ETHANOL AND WATER [J].

KAUFFMANN, T ;

ABELN, R ;

WINGBERMUHLE, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (09) :729-730

[10] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-7-DEACETOXYALCYONIN ACETATE - FIRST SYNTHESIS OF A EUNICELLIN DITERPENE [J].

MACMILLAN, DWC ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (41) :10391-10392

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