Synthesis of E-α,β-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride

被引：21

作者：

Concellón, JM ^{[1
]}

Rodríguez-Solla, H ^{[1
]}

Concellón, C ^{[1
]}

Díaz, P ^{[1
]}

机构：

[1] Univ Oviedo, Dipartimento Quim Organ & Inorgan, E-33006 Oviedo, Spain

来源：

SYNLETT | 2006年 / 06期

关键词：

alkenes; chromium; diastereoselectivity; samarium; ketones; sequential reactions;

D O I：

10.1055/s-2006-933146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

E-alpha,beta-Unsaturated ketones can be obtained with complete E-selectivity by a sequential reaction of dichloroketones with a variety of aldehydes. This transformation was promoted by SmI2, SmI2 in the presence of FeCl3 or CrCl2. The best results were obtained when CrCl2 was used as the metallating agent. A mechanism based on a successive aldol-type reaction and a beta-elimination is proposed to explain these results.

引用

页码：837 / 840

页数：4

共 11 条

[1] An easy, efficient, and completely stereoselective synthesis of (E)-α,β-unsaturated esters via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride
Concellón, JM
Concellón, C
Méjica, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (15): : 6111 - 6113
[2] Indium(I) bromide-promoted stereoselective preparation of (E)-α,β-unsaturated ketones via sequential intermolecular aldol-type coupling/elimination reactions of α,α-dichloroketones with aldehydes
Peppe, Clovis
das Chagas, Rafael Pavao
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (26) : 5856 - 5860
[3] Synthesis of (Z)-α(-chloro-α,β-unsaturated esters with complete stereoselectivity promoted by samarium diiodide
Concellón, JM
Huerta, M
Llavona, R
[J]. TETRAHEDRON LETTERS, 2004, 45 (24) : 4665 - 4667
[4] A Convenient Synthesis of (E)-α,β-Unsaturated Esters with Total Stereoselectivity Promoted by Catalytic Samarium Diiodide
Concellon, Jose M.
Rodriguez-Solla, Humberto
Concellon, Carmen
Diaz-Pardo, Ainhoa
Llavona, Ricardo
[J]. SYNLETT, 2011, (02) : 262 - 264
[5] An efficient synthesis of (E)-α,β-unsaturated ketones and esters with total stereoselectivity by using chromium dichloride
Concellón, JM
Rodríguez-Solla, H
Méjica, C
[J]. TETRAHEDRON, 2006, 62 (14) : 3292 - 3300
[6] Aldol-type reactions of unmasked iodoacetic acid with carbonyl compounds promoted by samarium diiodide:: Efficient synthesis of carboxylic 3-hydroxyacids and their derivatives
Concellon, Jose M.
Concellon, Carmen
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12): : 4428 - 4432
[7] Sequential elimination-reduction reactions promoted by samarium diiodide:: Synthesis of 2,3-dideuterioesters or -amides
Concellón, JM
Rodríguez-Solla, H
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (19) : 4266 - 4271
[8] Direct reaction of dibromoacetic acid with aldehydes promoted by samarium diiodide:: An easy, efficient, and rapid synthesis of (E)-α,β-unsaturated carboxylic acids with total stereoselectivity
Concellón, JM
Concellón, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04): : 1728 - 1731
[9] Sequential reactions promoted by manganese:: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids
Concellon, Jose M.
Rodriguez-Solla, Humberto
Diaz, Pamela
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21): : 7974 - 7979
[10] Highly selective synthesis of enantiopure (S,E)-α,β-unsaturated γ-amino esters through a sequential reaction of ethyl dibromoacetate with α-amino aldehydes promoted by chromium dichloride
Concellon, Jose M.
Mejica, Carmen
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (31) : 5250 - 5255

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