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

被引：28

作者：

Concellón, JM ^{[1
]}

Concellón, C ^{[1
]}

Méjica, C ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 15期

关键词：

D O I：

10.1021/jo050655o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(E)-alpha,beta-Unsaturated esters can be obtained with complete stereoselectivity by reaction of different aldehydes and ethyl dibromoacetate promoted by SmI2 or CrCl2. The transformation takes place as two sequential reactions: an aldol-type reaction and a P-elimination reaction.

引用

页码：6111 / 6113

页数：3

共 8 条

[1] Synthesis of E-α,β-unsaturated ketones with complete stereoselectivity via sequential aldol-type/elimination reactions promoted by samarium diiodide or chromium dichloride
Concellón, JM
Rodríguez-Solla, H
Concellón, C
Díaz, P
[J]. SYNLETT, 2006, (06) : 837 - 840
[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] 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
[4] Manganese-promoted β-elimination reactions:: Totally stereoselective synthesis of (E)-α,β-unsaturated esters
Concellón, JM
Rodríguez-Solla, H
del Amo, V
[J]. SYNLETT, 2006, (02) : 315 - 317
[5] 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
[6] 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
[7] 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
[8] Indium(I) bromide-promoted stereoselective preparation of cyclopropanes via sequential aldol-type coupling/elimination/Michael-induced ring closure reaction from α,α-dichloroacetophenone and aldehydes
Peppe, Clovis
das Chagas, Rafael Pavao
Burrow, Robert Alan
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (21-22) : 3441 - 3445

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