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

[1] REGIOSELECTIVE PALLADIUM(0) CATALYZED REDUCTION OF 1-ALKENYLCYCLOPROPYL ESTERS AS EQUIVALENT OF THE WITTIG REACTION
OLLIVIER, J
PIRAS, PP
STOLLE, A
AUFRANC, P
DEMEIJERE, A
SALAUN, J
TETRAHEDRON LETTERS, 1992, 33 (23) : 3307 - 3310
[2] PALLADIUM(0)-CATALYZED AZIDATION OF ALLYL ESTERS WITH TRIMETHYLSILYL AZIDE
SAFI, M
FAHRANG, R
SINOU, D
TETRAHEDRON LETTERS, 1990, 31 (04) : 527 - 530
[3] SYNTHESIS OF ALLYLSILANES BY PALLADIUM(0) CATALYZED REDUCTION OF TRIALKYLSILYLALLYL ESTERS
OLLIVIER, J
SALAUN, J
SYNLETT, 1994, (11) : 949 - 951
[4] REACTION OF ALLYL ACETATES AND KETENE SILYL ACETALS CATALYZED BY PALLADIUM(0) COMPLEXES .2. CYCLOPROPANATION VS ALLYLIC ALKYLATION
CARFAGNA, C
GALARINI, R
MUSCO, A
SANTI, R
JOURNAL OF MOLECULAR CATALYSIS, 1992, 72 (01): : 19 - 27
[5] PALLADIUM(0)-CATALYZED HYDROXYLAMINATION OF ALLYL ESTERS - SYNTHESIS OF N-ALLYLHYDROXYLAMINES AND SECONDARY ALLYLAMINES
MURAHASHI, S
IMADA, Y
TANIGUCHI, Y
KODERA, Y
TETRAHEDRON LETTERS, 1988, 29 (24) : 2973 - 2976
[6] PALLADIUM(0)-CATALYZED AZIDATION OF ALLYL ESTERS - SELECTIVE SYNTHESIS OF ALLYL AZIDES, PRIMARY ALLYLAMINES, AND RELATED-COMPOUNDS
MURAHASHI, SI
TANIGUCHI, Y
IMADA, Y
TANIGAWA, Y
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14): : 3292 - 3303
[7] PALLADIUM(0)-CATALYZED CARBONYLATION OF ALLYL PHOSPHATES AND ALLYL ACETATES - SELECTIVE SYNTHESIS OF BETA,GAMMA-UNSATURATED ESTERS
MURAHASHI, SI
IMADA, Y
TANIGUCHI, Y
HIGASHIURA, S
TETRAHEDRON LETTERS, 1988, 29 (39) : 4945 - 4948
[8] NEW CYCLOPROPYL BUILDING-BLOCKS FOR ORGANIC-SYNTHESIS .7. ON THE REGIOSELECTIVITY OF PALLADIUM(0)-CATALYZED SUBSTITUTIONS ON CYCLOPROPYL GROUP CONTAINING ALLYL ESTERS
STOLLE, A
SALAUN, J
DEMEIJERE, A
SYNLETT, 1991, (05) : 327 - 330
[9] PALLADIUM-CATALYZED PREPARATION OF ALPHA-ALLYL ESTERS AND ALPHA,BETA-UNSATURATED ESTERS FROM SATURATED ESTERS VIA THEIR KETENE SILYL ACETALS
TSUJI, J
TAKAHASHI, K
MINAMI, I
SHIMIZU, I
TETRAHEDRON LETTERS, 1984, 25 (42) : 4783 - 4786
[10] Preparation of Allyl and Vinyl Silanes by the Palladium-Catalyzed Silylation of Terminal Olefins: A Silyl-Heck Reaction
McAtee, Jesse R.
Martin, Sara E. S.
Ahneman, Derek T.
Johnson, Keywan A.
Watson, Donald A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) : 3663 - 3667

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