ALKYNYL PHENYL SELENIDES AS CONVENIENT PRECURSORS FOR THE SYNTHESIS OF STEREODEFINED TRISUBSTITUTED ALKENES

被引：79

作者：

TINGOLI, M

TIECCO, M

TESTAFERRI, L

TEMPERINI, A

PELIZZI, G

BACCHI, A

机构：

[1] UNIV PERUGIA,FAC FARM,IST CHIM ORGAN,I-06100 PERUGIA,ITALY

[2] UNIV PARMA,IST CHIM GEN & INORGAN,I-43100 PARMA,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 16期

关键词：

D O I：

10.1016/0040-4020(95)00153-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of p-toluensulfonic acid to alkynyl phenyl selenides is regio- and stereospecific and affords (Z)-alpha-(phenylseleno)vinyl p-toluensulfonates in good yield. alpha-(Phenylseleno)vinyl halides are obtained from the reactions of these compounds with magnesium halides. The reactions of (Z)-alpha-(phenylseleno)vinyl p-toluensulfonates with cyanocuprates afford the corresponding trisubstituted alkenes in which the tosyl group has been selectively substituted by an aryl or an alkyl group with retention of configuration. Finally, the cross coupling reaction of these vinyl selenides with methylmagnesium bromide, in the presence of a nickel catalyst, occurs with retention of configuration and affords the selenium free trisubstituted alkenes.

引用

页码：4691 / 4700

页数：10

共 21 条

[1]

Braga, Reckziegel, Silveira, Comasseto, Synth. Commun., 24, pp. 1165-1170, (1994)

[2]

Tingoli, Tiecco, Testaferri, Balducci, Reactions of Terminal Alkynes with Iodobenzene Diacetate and Diphenyl Diselenide: Synthesis of Phenyl Alkynyl Selenides, Synlett, pp. 211-212, (1993)

[3]

Back, Muralidharan, J. Org. Chem., 56, pp. 2781-2787, (1991)

[4]

Crisp, Meyer, Synthesis, pp. 667-668, (1994)

[5]

Radchenko, Zh. Org. Khim., 27, pp. 1597-1600, (1991)

[6]

Tingoli, Tiecco, Testaferri, Chianelli, Gazz. Chim. Ital., 121, pp. 59-61, (1991)

[7]

Martinez, Alvarez, Fraile, Herstellung von Vinyl-iodiden durch Umsetzung von Vinyl-triflaten mit Magnesiumiodid, Synthesis, pp. 222-224, (1986)

[8]

Scott, McMurry, Acc. Chem. Res., 21, pp. 47-54, (1988)

[9]

Lipshutz, Elworthy, J. Org. Chem., 55, pp. 1695-1696, (1990)

[10]

Lipshutz, Koerner, Parker, Tetrahedron Lett., 28, pp. 945-948, (1987)

← 1 2 3 →