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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3334-3339
Number of pages6
JournalTetrahedron
Volume63
Issue number16
DOIs
StatePublished - Apr 16 2007

Fingerprint

Ketones
Polymers
Catalysts

Keywords

  • CBS catalyst
  • Crosslinking monomer
  • Enantioselective reduction
  • Polymer beads
  • Polymer disks

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Varela, M. C., Dixon, S. M., Price, M. D., Merit, J. E., Berget, P. E., Shiraki, S., ... Schore, N. E. (2007). Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts. Tetrahedron, 63(16), 3334-3339. https://doi.org/10.1016/j.tet.2007.02.048

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 journalArticle

Varela, MC, Dixon, SM, Price, MD, Merit, JE, Berget, PE, Shiraki, S, Kurth, MJ & Schore, NE 2007, 'Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts', Tetrahedron, vol. 63, no. 16, pp. 3334-3339. https://doi.org/10.1016/j.tet.2007.02.048
Varela, Michael C. ; Dixon, Seth M. ; Price, Michael D. ; Merit, Jeffrey E. ; Berget, Patrick E. ; Shiraki, Saori ; Kurth, Mark J. ; Schore, Neil E. / Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts. In: Tetrahedron. 2007 ; Vol. 63, No. 16. pp. 3334-3339.
@article{d0fa7a8817b647a7b20d0d3b48759a36,
title = "Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts",
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.",
keywords = "CBS catalyst, Crosslinking monomer, Enantioselective reduction, Polymer beads, Polymer disks",
author = "Varela, {Michael C.} and Dixon, {Seth M.} and Price, {Michael D.} and Merit, {Jeffrey E.} and Berget, {Patrick E.} and Saori Shiraki and Kurth, {Mark J.} and Schore, {Neil E.}",
year = "2007",
month = "4",
day = "16",
doi = "10.1016/j.tet.2007.02.048",
language = "English (US)",
volume = "63",
pages = "3334--3339",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",

}

TY - JOUR

T1 - Comparison of enantioselective reductions using bead and monolith 'disk' polymer formulations of CBS catalysts

AU - Varela, Michael C.

AU - Dixon, Seth M.

AU - Price, Michael D.

AU - Merit, Jeffrey E.

AU - Berget, Patrick E.

AU - Shiraki, Saori

AU - Kurth, Mark J.

AU - Schore, Neil E.

PY - 2007/4/16

Y1 - 2007/4/16

N2 - 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.

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.

KW - CBS catalyst

KW - Crosslinking monomer

KW - Enantioselective reduction

KW - Polymer beads

KW - Polymer disks

UR - http://www.scopus.com/inward/record.url?scp=33947219450&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947219450&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2007.02.048

DO - 10.1016/j.tet.2007.02.048

M3 - Article

AN - SCOPUS:33947219450

VL - 63

SP - 3334

EP - 3339

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 16

ER -