Catalytic alkylation reactions of weakly acidic carbonyl and related compounds using alkenes as electrophiles

被引：21

作者：

Yamashita, Yasuhiro ^{[1
]}

Igarashi, Ryo ^{[1
]}

Suzuki, Hirotsugu ^{[1
]}

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 33期

基金：

日本科学技术振兴机构; 日本学术振兴会;

关键词：

POTASSIUM TERT-BUTOXIDE; 1,4-ADDITION REACTIONS; ALPHA-ALKYLATION; CONJUGATE ADDITIONS; DUAL ACTIVATION; SIMPLE OLEFINS; ATOM ECONOMY; DERIVATIVES; ALDEHYDES; KETONES;

D O I：

10.1039/c8ob00941d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic alkylation reactions of weakly acidic carbonyl and related pronucleophiles such as amides, esters, and sulfonamides with substituted alkenes have been reported. In the presence of a strong Bronsted base catalyst system, potassium hexamethyldisilazide and 18-crown-6 ether, the desired reactions proceeded in high yields at ambient temperature with a wide substrate scope. These are atomeconomical catalytic alkylation reactions of carbonyl and related compounds.

引用

页码：5969 / 5972

页数：4

共 37 条

[1]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[2] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[3]

Anastas P.T., 2009, Handbook of green chemistry

[4] Lithium-iodine exchange mediated atom transfer cyclization: Catalytic cycloisomerization of 6-iodo-1-hexenes [J].

Bailey, WF ;

Carson, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :361-365

[5] Catalytic cycloisomerization of unsaturated organoiodides [J].

Bailey, WF ;

Carson, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9960-9967

[6] Enantioselective organocatalysis using SOMO activation [J].

Beeson, Teresa D. ;

Mastracchio, Anthony ;

Hong, Jun-Bae ;

Ashton, Kate ;

MacMillan, David W. C. .

SCIENCE, 2007, 316 (5824) :582-585

[7]

Caine D., 1991, Comprehensive Organic Synthesis, V3, P1, DOI DOI 10.1016/B978-0-08-052349-1.00058-5

[8] Direct, enantioselective α-alkylation of aldehydes using simple olefins [J].

Capacci, Andrew G. ;

Malinowski, Justin T. ;

McAlpine, Neil J. ;

Kuhne, Jerome ;

MacMillan, David W. C. .

NATURE CHEMISTRY, 2017, 9 (11) :1073-1077

[9] Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].

Christoffers, J ;

Baro, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690

[10] Recent advances in metal-catalyzed asymmetric conjugate additions [J].

Christoffers, Jens ;

Koripelly, Girish ;

Rosiak, Anna ;

Roessle, Michael .

SYNTHESIS-STUTTGART, 2007, (09) :1279-1300

← 1 2 3 4 →