Functionalized Cross-Linked Copolymers: A “C2-Symmetric” Solid-Phase Catalyst for Enantioselective Reactions

Halm, Chris; Kurth, Mark J.

doi:10.1002/(sici)1521-3773(19980302)37:4<510::aid-anie510>3.0.co;2-9

Cited by 55 publications

(2 citation statements)

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“…118 The incorporation of the catalytic ligand at the resin cross link has recently been investigated. 119 (R,R)-1,2-diaminocyclohexane was functionalized with sty-renesulfonyl chloride and then copolymerized with styrene to afford resin with the ligand incorporated at the cross link. The resin was used in enantioselective alkylation of aldehydes and cyclopropanation of allylic alcohols and produced enantiomeric excesses slightly below the values obtained in solution.…”

Section: P O L Y M E R -S U P P O R T E D C a T A L Y S T S A N D M E T A L Smentioning

confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

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The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

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Section: P O L Y M E R -S U P P O R T E D C a T A L Y S T S A N D M E T A L Smentioning

confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

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“…Most solid-supported syntheses utilize polystyrene that is cross-linked with 1−2% divinylbenzene as the support. In the vast majority of cases, the linker functionality is attached to the phenyl rings of the pre-polymerized polystyrene-divinylbenzene beads via chemical reactions. 1b, Alternatively, selected functional styrenes have been employed and used in suspension polymerization to create polystyrene resins with desirable linker functionality . A major requirement of this latter technique is that the functional monomers neither react with nor dissolve in water, the most frequently used suspending solvent.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Designer Resins via Living Free Radical Polymerization of Functional Monomers on Solid Support

Hodges¹,

Harikrishnan²,

Ault-Justus³

1999

J. Comb. Chem.

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Merrifield resin is converted to a solid-supported free radical initiator by reacting with the TEMPO-Na. Heating TEMPO-methyl resin with a variety of functionalized styrene and acrylate monomers gives larger resin beads via living free radical polymerization. We have coined the term Rasta resin to describe resin beads prepared in this fashion. The process can be described as a solvent-free suspension polymerization. It is particularly well suited for preparation of resin beads from monomers which contain electrophilic groups that would be destroyed upon suspension polymerization in water. Rasta resins have a novel macromolecular architecture wherein long straight chain polymers bearing reactive functional groups emanate from the phenyl groups of a cross-linked polystyrene core. With judicious choice of co-monomers and polymerization strategy, the solvent affinity, loading capacity, and distance of functionality from the cross-linked core may be controlled giving beads with properties that are tailored to specific uses as synthesis supports and scavenging resins.

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