Enantioselective Diels-Alder reactions: room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

Takacs, James M.; Lawson, Edward C.; Reno, J. Michael; Youngman, Mark A.; Quincy, David A.

doi:10.1016/s0957-4166(97)00322-4

Cited by 51 publications

(17 citation statements)

References 19 publications

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“…The first examples of enantioselective zinc-catalyzed (hetero)-Diels-Alder cycloadditions were independently reported in 1997 by the groups of Takacs [15] and Jørgensen [16] who both employed chiral bisoxazoline ligands, allowing similar enantioselectivities of 78-79% ee to be achieved. Ever since, other types of ligands have been successfully investigated in these reactions [4].…”

Section: Diels-alder Cycloadditionsmentioning

confidence: 99%

Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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This review collects the recent advances in the field of enantioselective zinc-catalyzed transformations, covering the literature since the beginning of 2015, illustrating the power of chiral green zinc catalysts to promote all types of reactions. A range of highly enantioselective reactions have been developed in the last six years, including cycloadditions, alkynylation/allylation reactions of carbonyl compounds and derivatives, additions of diorganozincs to carbonyl compounds and derivatives, Mannich reactions, (nitro)aldol reactions, other 1,2-nucleophilic additions to carbonyl compounds and derivatives, Michael additions, Friedel-Crafts reactions, reductions, a-functionalizations of carbonyl compounds, ringopening reactions, epoxidations, halolactonizations, domino/tandem reactions and miscellaneous reactions.

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Section: Diels-alder Cycloadditionsmentioning

confidence: 99%

Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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“…1). Besides the central chirality element in the oxazoline moiety, these ligands possess an additional chirality element in the backbone such as 1,3-dioxolane I, [10][11][12] bicyclo [2,2,1] II, [2,2,2] III, 13 cyclohexane IV, 14,15 and cyclopentane V. Although the Diels-Alder reaction between acrylimide dienophiles and cyclopentadiene was the most successful application of the Cu(II)-bis(oxazoline) catalytic system with enantiomeric excess up to 99%, [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] its application with the ligands I, II, III, IV and V was less effective in enantioselectivity. In particular, the ligand III, previously introduced by Takacs et al, 13 has particularly focused our attention since the best enantioselectivity (75%) in the Diels-Alder reaction surprisingly involves the meso-backbone and poor results were obtained with the other chiral configurations.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric copper-catalyzed Diels–Alder reaction revisited: control of the structure of bis(oxazoline) ligands

Maux¹,

Dorcet²,

Simonneaux³

2013

Tetrahedron

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To cite this version:Paul Le Maux, Vincent Dorcet, Gérard Simonneaux. Asymmetric copper-catalyzed Diels-Alder reaction revisited: control of the structure of bis(oxazoline) ligands. Tetrahedron, Elsevier, 2013, 69 (38) AbstractSynthesis of 1,4-bis(oxazoline) ligands bearing a bicyclo[2,2,2]backbone derived from 9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid was revisited. Starting from L-or D-amino alcohols and either (S,S) or (R,R)-dihydroethano trans-dicarboxylic acid, a complete series of ligands was evaluated in the copper-catalyzed Diels-Alder reaction. The most efficient ligands with a phenyl substituent on the oxazoline ring afforded enantiomeric excess up to 98%. This is different from previous results indicating that the best enantioselectivity involved a diastereomeric ligand with the meso-backbone.

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“…1). In order to test the influence of the side chain at 2-position of chiral oxazolines, we examined the Lewis acid-catalyzed Diels-Alder reactions of well-used 3-(2-propenoyl)-1,3-oxazolidin-2-one 8 [18][19][20][21][22] as a dienophile with cyclopentadiene using moxes 2-6 as chiral ligands.…”

mentioning

confidence: 99%

“…The opposite enantiomer should be formed via a square-planar complex analogous to box 6c-copper-7 complex proposed by Evans. 6,24) or an octahedral complex 22) like 1.…”

mentioning

confidence: 99%

The Influence of Ligand Side Chain on the Enantioselectivity of Lewis Acid Catalyzed Diels-Alder Reactions.

Yamauchi

Itai

Honda

2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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The enantioselective Lewis acid-catalyzed Diels-Alder reaction of 3-(2-propenoyl)-1,3-oxazolidin-2-one 8 with cyclopentadiene was examined using a series of chiral mox ligands 2-6, deferring in the side chain at 2-position of the chiral oxazoline and in the nature of the substituent at the chiral center (4-position) of the oxazoline ring, and a combination of N-[(1R)-2-chloro-1-phenylethyl]-2-[(4R)-4-phenyl-4,5-dihydrooxazol-2-yl]butyramide 2-MgI 2 -I 2 was the most efficient catalyst.

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Enantioselective Diels-Alder reactions: room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts

Cited by 51 publications

References 19 publications

Recent developments in enantioselective zinc-catalyzed transformations

Recent developments in enantioselective zinc-catalyzed transformations

Asymmetric copper-catalyzed Diels–Alder reaction revisited: control of the structure of bis(oxazoline) ligands

The Influence of Ligand Side Chain on the Enantioselectivity of Lewis Acid Catalyzed Diels-Alder Reactions.

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