Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts

Michael C. Varela; Seth M. Dixon; Michael D. Price; Jeffrey E. Merit; Patrick E. Berget; Saori Shiraki; Mark J. Kurth; Neil E. Schore

doi:10.1016/j.tet.2007.02.048

Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts

Michael C. Varela, Seth M. Dixon, Michael D. Price, Jeffrey E. Merit, Patrick E. Berget, Saori Shiraki, Mark J. Kurth, Neil E. Schore

Chemistry

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

10 Scopus citations

Abstract

Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly.

Original language	English (US)
Pages (from-to)	3334-3339
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2007.02.048
State	Published - Apr 16 2007

Keywords

CBS catalyst
Crosslinking monomer
Enantioselective reduction
Polymer beads
Polymer disks

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tet.2007.02.048

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Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts. / Varela, Michael C.; Dixon, Seth M.; Price, Michael D.; Merit, Jeffrey E.; Berget, Patrick E.; Shiraki, Saori; Kurth, Mark J.; Schore, Neil E.

In: Tetrahedron, Vol. 63, No. 16, 16.04.2007, p. 3334-3339.

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

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AU - Price, Michael D.

AU - Merit, Jeffrey E.

AU - Berget, Patrick E.

AU - Shiraki, Saori

AU - Kurth, Mark J.

AU - Schore, Neil E.

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AB - Two polymer-supported versions of the Corey, Bakshi, and Shibata (CBS) catalyst were prepared and examined. Polymeric beads, with the auxiliary bound in pendant and crosslinked fashion, were prepared utilizing an improved procedure based upon earlier work. Optimization of a procedure for ketone reduction gives results that match those in solution. Attempted reuse gave mixed results. For comparison purposes, CBS functionalized monoliths were formed and tested but performed poorly.

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KW - Crosslinking monomer

KW - Enantioselective reduction

KW - Polymer beads

KW - Polymer disks

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Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts

Abstract

Keywords

ASJC Scopus subject areas

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