A New Polymer-Anchored Chiral Catalyst for Asymmetric Michael Addition Reactions

G. Sundararajan; N. Prabagaran

doi:10.1021/ol006898e

A New Polymer-Anchored Chiral Catalyst for Asymmetric Michael Addition Reactions

G. Sundararajan, N. Prabagaran

Research output: Contribution to journal › Article › peer-review

120 Scopus citations

Abstract

(Equation Presented) Monomer (R,R)-3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane (2) when polymerized with styrene and divinylbenzene affords polymers, onto which lithium and aluminum are incorporated via reaction with lithium aluminum hydride. The resulting insoluble polymers containing chiral lithium and aluminum active centers are quite effective for asymmetric Michael addition of nitro compounds, thiols, and amines. The optimized reaction conditions yield Michael adducts in good yield with high enantiomeric excesses.

Original language	English (US)
Pages (from-to)	389-392
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	3
DOIs	https://doi.org/10.1021/ol006898e
State	Published - Feb 8 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Equation Presented) Monomer (R,R)-3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane (2) when polymerized with styrene and divinylbenzene affords polymers, onto which lithium and aluminum are incorporated via reaction with lithium aluminum hydride. The resulting insoluble polymers containing chiral lithium and aluminum active centers are quite effective for asymmetric Michael addition of nitro compounds, thiols, and amines. The optimized reaction conditions yield Michael adducts in good yield with high enantiomeric excesses.",

author = "G. Sundararajan and N. Prabagaran",

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doi = "10.1021/ol006898e",

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N2 - (Equation Presented) Monomer (R,R)-3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane (2) when polymerized with styrene and divinylbenzene affords polymers, onto which lithium and aluminum are incorporated via reaction with lithium aluminum hydride. The resulting insoluble polymers containing chiral lithium and aluminum active centers are quite effective for asymmetric Michael addition of nitro compounds, thiols, and amines. The optimized reaction conditions yield Michael adducts in good yield with high enantiomeric excesses.

AB - (Equation Presented) Monomer (R,R)-3-aza-3-(p-vinylbenzyl)-1,5-diphenyl-1,5-dihydroxypentane (2) when polymerized with styrene and divinylbenzene affords polymers, onto which lithium and aluminum are incorporated via reaction with lithium aluminum hydride. The resulting insoluble polymers containing chiral lithium and aluminum active centers are quite effective for asymmetric Michael addition of nitro compounds, thiols, and amines. The optimized reaction conditions yield Michael adducts in good yield with high enantiomeric excesses.

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A New Polymer-Anchored Chiral Catalyst for Asymmetric Michael Addition Reactions

Abstract

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