Palladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral γ-Butyrolactones

被引：27

作者：

Stockton, Kieran P. ^{[1
]}

Merritt, Christopher J. ^{[1
]}

Sumby, Christopher J. ^{[2
]}

Greatrex, Ben W. ^{[1
]}

机构：

[1] Univ New England, Sch Sci & Technol, Armidale, NSW, Australia

[2] Univ Adelaide, Sch Phys Sci, Dept Chem, Adelaide, SA, Australia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 32期

关键词：

Homogeneous catalysis; Lactones; Cross-coupling; Levoglucosenone; Chiral pool; CROSS-COUPLING REACTIONS; CONJUGATE ADDITION; FORMAL SYNTHESIS; ARYL; LEVOGLUCOSENONE; LIGAND; ACID; DERIVATIVES; LACTONES; HALIDES;

D O I：

10.1002/ejoc.201501083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral pool material (-)-levoglucosenone (6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, LGO) has been substituted by using a series of Pd-mediated cross-coupling reactions. Iodination of LGO followed by Suzuki-Miyaura cross-coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)(2) afforded 3-aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2-position was achieved with aryl iodides with K3PO4 as base and SPhos ligand with Pd(OAc)(2) (1-5 mol-%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd(OAc)(2), and P(o-tol)(3). The products were converted, either directly or after alkene reduction, through a Baeyer-Villiger oxidation into chiral 3- and 4-substituted 5-(hydroxymethyl)dihydrofuran-2(3H)-ones.

引用

页码：6999 / 7008

页数：10

共 49 条

[1] The FEMA GRAS assessment of lactones used as flavour ingredients
Adams, TB
Greer, DB
Doull, J
Munro, IC
Newberne, P
Portoghese, PS
Smith, RL
Wagner, BM
Weil, CS
Woods, LA
Ford, RA
[J]. FOOD AND CHEMICAL TOXICOLOGY, 1998, 36 (04) : 249 - 278
[2] CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS
AMORESE, A
ARCADI, A
BERNOCCHI, E
CACCHI, S
CERRINI, S
FEDELI, W
ORTAR, G
[J]. TETRAHEDRON, 1989, 45 (03) : 813 - 828
[3] [Anonymous], NEW TRENDS CROSS COU
[4] The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides
Awad, Loay
Demange, Raynald
Zhu, Yao-Hua
Vogel, Pierre
[J]. CARBOHYDRATE RESEARCH, 2006, 341 (10) : 1235 - 1252
[5] Tin-assisted cyclization for chiral cyclohexane synthesis, an alternative route to (-)-tetrodotoxin skeleton
Bamba, M
Nishikawa, T
Isobe, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (45) : 8199 - 8202
[6] Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189, DOI 10.1016/S1472-7862(02)00030-8
[7] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
Barder, TE
Walker, SD
Martinelli, JR
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
[8] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
CABRI, W
CANDIANI, I
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
[9] PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF ARYL IODIDES WITH ALPHA,BETA-UNSATURATED KETONES
CACCHI, S
ARCADI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) : 4236 - 4240
[10] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
DE MEIJERE, A
MEYER, FE
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411

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