STRAIN, SILYL AND STERIC EFFECTS ON THE REGIOSELECTIVITY OF PALLADIUM(0) CATALYZED ALLYL ESTERS REDUCTION AS ALTERNATIVE TO THE WITTIG REACTION

被引：26

作者：

OLLIVIER, J

DORIZON, P

PIRAS, PP

DEMEIJERE, A

SALAUN, J

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,W-3400 GOTTINGEN,GERMANY

[2] UNIV PARIS 11,INST CHIM MOLEC ORSAY,CNRS,CARBOCYCLES LAB,F-91405 ORSAY,FRANCE

[3] UNIV CAGLIARI,DIPARTIMENTO SCI CHIM,I-09124 CAGLIARI,ITALY

来源：

INORGANICA CHIMICA ACTA | 1994年 / 222卷 / 1-2期

关键词：

CATALYSIS; REDUCTIVE CLEAVAGE; PALLADIUM COMPLEXES; ALLYL COMPLEXES; STERIC EFFECTS;

D O I：

10.1016/0020-1693(94)03892-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1-(1-alkenyl)- (1a-g) and 1-(1-cycloalkenyl)cycloalkyl esters (acetate, tosylate, mesylate) (4a-d) underwent palladium(0) catalyzed hydrogenolysis by sodium formate or n-butylzinc chloride as hydride sources. The regioselectivity of the reduction can be monitored either by ring strain, silyl substitution of the allyl moieties or by using the steric effect of trivalent phosphorus ligands related to their cone angles theta. Alkylidenecycloalkanes (2a-g) and cycloalkylidenecycloalkanes (5a-d) have been obtained, generally in good yields, thus providing a convenient alternative to the Wittig olefination and a new access to allylsilanes.

引用

页码：37 / 49

页数：13

共 32 条

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