Reductive dehydroxylation of Baylis-Hillman adducts with low-valent titanium reagent: syntheses of stereoselective trisubstituted alkenes

被引：28

作者：

Shadakshari, U ^{[1
]}

Nayak, SK ^{[1
]}

机构：

[1] Bhabha Atom Res Ctr, Div Bioorgan, Mumbai 400085, India

来源：

TETRAHEDRON | 2001年 / 57卷 / 21期

关键词：

Baylis-Hillman; low-valent titanium; dehydroxylation; trisubstituted alkene;

D O I：

10.1016/S0040-4020(01)00333-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Baylis-Hillman adducts prepared from aromatic aldehydes and methyl acrylate underwent smooth dehydroxylation with concomitant olefin isomerisation with low-valent titanium reagent to provide the trisubstituted alkenes with high (E)-selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4599 / 4602

页数：4

共 16 条

[1]

AKIRA K, 1989, J HETEROCYCLIC CHEM, V26, P597

[2] Total synthesis of (-)-hemiasterlin, a structurally novel tripeptide that exhibits potent cytotoxic activity [J].

Andersen, RJ ;

Coleman, JE ;

Piers, E ;

Wallace, DJ .

TETRAHEDRON LETTERS, 1997, 38 (03) :317-320

[3] Influence of external ligands and auxiliaries on the reactivity of low-valent titanium in McMurry reaction: Selectivity and mechanistic profile [J].

Balu, N ;

Nayak, SK ;

Banerji, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (25) :5932-5937

[4] The Friedel-Crafts reaction of the Baylis-Hillman adducts [J].

Basavaiah, D ;

Krishnamacharyulu, M ;

Hyma, RS ;

Pandiaraju, S .

TETRAHEDRON LETTERS, 1997, 38 (12) :2141-2144

[5]

Ciganek E., 1997, ORG REACTIONS, V51, P201

[6] Total synthesis of phenoxan and a related pyrone derivative [J].

Ishibashi, Y ;

Ohba, S ;

Nishiyama, S ;

Yamamura, S .

TETRAHEDRON LETTERS, 1996, 37 (17) :2997-3000

[7] LOW-VALENT TITANIUM - A NEW APPROACH TO DEPROTECTION OF ALLYL AND BENZYL GROUPS [J].

KADAM, SM ;

NAYAK, SK ;

BANERJI, A .

TETRAHEDRON LETTERS, 1992, 33 (35) :5129-5132

[8] CARBONYL-COUPLING REACTIONS USING LOW-VALENT TITANIUM [J].

MCMURRY, JE .

CHEMICAL REVIEWS, 1989, 89 (07) :1513-1524

[9] SIMPLIFIED METHOD FOR TITANIUM(II)-INDUCED COUPLING OF ALLYLIC AND BENZYLIC ALCOHOLS [J].

MCMURRY, JE ;

SILVESTRI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (18) :2687-2688

[10] FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S [J].

NAGAOKA, H ;

KISHI, Y .

TETRAHEDRON, 1981, 37 (23) :3873-3888

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