Synthesis and reactivity of beta-phenylselanyl alpha-oxoesters

被引：14

作者：

Boivin, S ^{[1
]}

Outurquin, F ^{[1
]}

Paulmier, C ^{[1
]}

机构：

[1] UNIV ROUEN,UFR SCI & TECH,LAB SYNTHESE THIO & SELENOORGAN IRCOF,F-76821 MONT ST AIGNAN,FRANCE

来源：

TETRAHEDRON | 1997年 / 53卷 / 49期

关键词：

D O I：

10.1016/S0040-4020(97)10117-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Phenylselanyl alpha-oxoesters 2 were prepared by N-phenylselanyl morpholine treatment of alpha-oxoesters 1, oxidized into beta-unsaturated alpha-oxoesters 5 and subjected to the Wittig-Horner olefination. The diethyl (1-phenylselanylalkyl)maleates 6 have led, after [2,3]sigmatropic rearrangement of the corresponding selenoxides, to the diethyl 3-alkylidene-2-hydroxysuccinates 7. The 2-(t-butoxycarbonylamino)-3-alkylidenesuccinates 8 were prepared in a similar way. The decomposition of halo-adducts derived from compounds 6 has allowed the synthesis of the diethyl 3-alkylidene-2-halosuccinates 9 and 10. (C) 1997 Elsevier Science Ltd.

引用

页码：16767 / 16782

页数：16

共 35 条

[1] KINETIC RESOLUTION IN THE DIRECTED HYDROGENATION OF N-SUBSTITUTED ALPHA-(AMINOALKYL) ACRYLATES, PRECURSORS OF OPTICALLY-ACTIVE BETA-AMINO ACIDS [J].

BROWN, JM ;

JAMES, AP ;

PRIOR, LM .

TETRAHEDRON LETTERS, 1987, 28 (19) :2179-2182

[2] N-(PHENYLSELENO)PHTHALIMIDE - A USEFUL REAGENT FOR THE ALPHA-SELENYLATION OF KETONES AND ALDEHYDES [J].

COSSY, J ;

FURET, N .

TETRAHEDRON LETTERS, 1993, 34 (48) :7755-7756

[3] STUDY OF THE DECOMPOSITION OF HALO ADDUCTS DERIVED FROM PROPARGYLIC PHENYLSELENIDES - INTERMEDIATE FORMATION OF HALOALLENES [J].

DUCLOS, JF ;

OUTURQUIN, F ;

PAULMIER, C .

TETRAHEDRON LETTERS, 1995, 36 (15) :2627-2630

[4] SYNTHESIS OF ALPHA-HALO BETA,GAMMA-UNSATURATED ESTERS FROM GAMMA-PHENYLSELENO ALPHA,BETA-UNSATURATED ESTERS [J].

DUCLOS, JF ;

OUTURQUIN, F ;

PAULMIER, C .

TETRAHEDRON LETTERS, 1993, 34 (46) :7417-7420

[5] SYNTHESIS OF PROTECTED ALLYLIC AMINES FROM ALLYLIC PHENYL SELENIDES - IMPROVED CONDITIONS FOR THE CHLORAMINE-T OXIDATION OF ALLYLIC PHENYL SELENIDES [J].

FANKHAUSER, JE ;

PEEVEY, RM ;

HOPKINS, PB .

TETRAHEDRON LETTERS, 1984, 25 (01) :15-18

[6] SYNTHESIS OF PROTECTED RACEMIC BETA,GAMMA-UNSATURATED-ALPHA-AMINO ACIDS VIA GAMMA-PHENYLSELENO-ALPHA,BETA-UNSATURATED ESTERS [J].

FITZNER, JN ;

PRATT, DV ;

HOPKINS, PB .

TETRAHEDRON LETTERS, 1985, 26 (16) :1959-1962

[7] ASYMMETRIC CARBON TO NITROGEN BOND FORMATION USING OPTICALLY-ACTIVE ALLYLIC SELENIDES - A NEW GENERAL-METHOD FOR THE SYNTHESIS OF N-PROTECTED OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].

FITZNER, JN ;

SHEA, RG ;

FANKHAUSER, JE ;

HOPKINS, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (03) :417-419

[8] ALPHA-TETRONIC ACIDS + 3,6-DIHYDRO-2H-1,3-THIAZINE RING [J].

GREEN, DM ;

LONG, AG ;

TURNER, AF ;

MAY, PJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (FEB) :766-&

[9]

HIROI K, 1986, SYNTHESIS-STUTTGART, P635

[10]

Houllemare D, 1997, SYNTHESIS-STUTTGART, P101

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