Pyranoside phosphite-phosphoroamidite ligands for Pd-catalyzed asymmetric allylic alkylation reactions

被引：17
作者：
Mata, Yvette [1 ]
Claver, Carmen [1 ]
Dieguez, Montserrat [1 ]
Pamies, Oscar [1 ]
机构：
[1] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43007, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 23期
关键词：
D O I：
10.1016/j.tetasy.2006.11.039
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
We have designed and synthesized a new family of readily available phosphite-phosphoroamidite ligands for Pd-catalyzed allylic substitution reactions of several substrates with different steric and electronic properties. These ligands are derived from D-glucosamine and contain several substituents in the biphenyl moieties, with different steric and electronic properties. Systematic variation of the ligand parameters indicates that enantioselectivities are mainly affected by the substituents at the para-positions of the biphenyl moieties. Enantiomeric excesses of up to 89% with high activities were obtained for rac-1,3-diphenyl-3-acetoxyprop-1-ene S1, rac-(E)-ethyl -2,5-dimethyl-3-hex-4-enyl carbonate S2 and rac-3-acetoxycycloheptene S5. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3282 / 3287
页数：6
相关论文
共 34 条
  • [1] A new P,S-Chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand
    Albinati, A
    Pregosin, PS
    Wick, K
    [J]. ORGANOMETALLICS, 1996, 15 (10) : 2419 - 2421
  • [2] ASYMMETRIC-SYNTHESIS - ASYMMETRIC CATALYTIC ALLYLATION USING PALLADIUM CHIRAL PHOSPHINE COMPLEXES
    AUBURN, PR
    MACKENZIE, PB
    BOSNICH, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (07) : 2033 - 2046
  • [3] New chiral N,S-ligands based on oxazoline-thioglucose donors. Palladium(II)-catalyzed enantioselective allylic alkylation
    Boog-Wick, K
    Pregosin, PS
    Trabesinger, G
    [J]. ORGANOMETALLICS, 1998, 17 (15) : 3254 - 3264
  • [4] RHODIUM-CATALYZED ASYMMETRIC HYDROFORMYLATION WITH CHIRAL DIPHOSPHITE LIGANDS
    BUISMAN, GJH
    KAMER, PCJ
    VANLEEUWEN, PWNM
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1625 - 1634
  • [5] Chiral cooperativity in diastereomeric diphosphite ligands: Effects on the rhodium-catalyzed enantioselective hydroformylation of styrene
    Buisman, GJH
    vanderVeen, LA
    Klootwijk, A
    deLange, WGJ
    Kamer, PCJ
    vanLeeuwen, PWNM
    Vogt, D
    [J]. ORGANOMETALLICS, 1997, 16 (13) : 2929 - 2939
  • [6] Ligands derived from carbohydrates for asymmetric catalysis
    Diéguez, M
    Pàmies, OP
    Claver, C
    [J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3189 - 3215
  • [7] Modular furanoside diphosphite ligands for Pd-catalyzed asymmetric allylic substitution reactions:: Scope and limitations
    Diéguez, M
    Pàmies, O
    Claver, C
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (09) : 1257 - 1266
  • [8] Palladium-diphosphite catalysts for the asymmetric allylic substitution reactions
    Diéguez, M
    Pàmies, O
    Claver, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3363 - 3368
  • [9] Carbohydrate derivative ligands in asymmetric catalysis
    Diéguez, M
    Pàmies, O
    Ruiz, A
    Díaz, Y
    Castillón, S
    Claver, C
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2165 - 2192
  • [10] Recent advances in Rh-catalyzed asymmetric hydroformylation using phosphite ligands
    Diéguez, M
    Pàmies, O
    Claver, C
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2113 - 2122
1234