Ethyl(benzothiazol-2-ylsulfonyl)acetate:: a new reagent for the stereoselective synthesis of α,β-unsaturated esters from aldehydes

被引：59

作者：

Blakemore, PR ^{[1
]}

Ho, DKH ^{[1
]}

Nap, WM ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 08期

关键词：

D O I：

10.1039/b500713e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title reagent engaged in the modified Julia olefination with aldehydes under mild reaction conditions (DBU, CH2Cl2, rt or -78 degrees C) to yield alpha,beta-unsaturated esters; aryl aldehydes and aliphatic aldehydes possessing significant chain branching elements gave trans alkene products with high stereoselectivity (E : Z up to >98 : 2), while straight chain aliphatic aldehydes gave cis products preferentially (Z : E up to 92 : 8).

引用

页码：1365 / 1368

页数：4

共 24 条

[1] 3,5-bis(trifluoromethyl)phenyl sulfones in the modified Julia olefination:: application to the synthesis of resveratrol [J].

Alonso, DA ;

Nájera, C ;

Varea, M .

TETRAHEDRON LETTERS, 2004, 45 (03) :573-577

[2] Z-selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU [J].

Ando, K ;

Oishi, T ;

Hirama, M ;

Ohno, H ;

Ibuka, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4745-4749

[3] PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE [J].

ANDO, K .

TETRAHEDRON LETTERS, 1995, 36 (23) :4105-4108

[4] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].

BAUDIN, JB ;

HAREAU, G ;

JULIA, SA ;

RUEL, O .

TETRAHEDRON LETTERS, 1991, 32 (09) :1175-1178

[5]

BAUDIN JB, 1993, B SOC CHIM FR, V130, P856

[6] The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].

Blakemore, PR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585

[7]

Blakemore PR, 1998, SYNLETT, P26

[8] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[9] An expedient approach to E,Z-dienes using the Julia olefination (vol 42, pg 5149, 2001) [J].

Charette, AB ;

Berthelette, C ;

St-Martin, D .

TETRAHEDRON LETTERS, 2001, 42 (37) :6619-6619

[10] Synthesis of microcarpalide, a microfilament disrupting agent [J].

Ishigami, K ;

Kitahara, T .

HETEROCYCLES, 2004, 63 (04) :785-790

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