Highly asymmetric heterogeneous catalytic hydrogenation of isophorone on proline modified base-supported palladium catalysts

Shilpa C. Mhadgut; Marianna Török; Joseph Esquibel; Béla Török

doi:10.1016/j.jcat.2006.01.004

Highly asymmetric heterogeneous catalytic hydrogenation of isophorone on proline modified base-supported palladium catalysts

Shilpa C. Mhadgut
, Marianna Török
, Joseph Esquibel
, Béla Török

Chemistry

University of Massachusetts Boston
Michigan Technological University
Massachusetts Institute of Technology

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

Abstract

A highly effective asymmetric heterogeneous catalytic hydrogenation of isophorone (3,5,5-trimethyl-2-cyclohexenone) by proline-modified base-supported Pd catalysts is described. Effective combination of enhanced proline adsorption and secondary kinetic resolution resulted in very high enantioselectivities (ee up to 99%). Using (S)- and (R)-proline enantiomers as chiral auxiliaries, both enantiomers of the product were obtained with excellent optical yields.

Original language	English
Pages (from-to)	441-448
Number of pages	8
Journal	Journal of Catalysis
Volume	238
Issue number	2
DOIs	https://doi.org/10.1016/j.jcat.2006.01.004
State	Published - Mar 10 2006

ASJC Scopus Subject Areas

Catalysis
Physical and Theoretical Chemistry

Keywords

Chiral hydrogenation
Isophorone
Pd catalysts
Proline
Secondary kinetic resolution
Support effect

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10.1016/j.jcat.2006.01.004

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title = "Highly asymmetric heterogeneous catalytic hydrogenation of isophorone on proline modified base-supported palladium catalysts",

abstract = "A highly effective asymmetric heterogeneous catalytic hydrogenation of isophorone (3,5,5-trimethyl-2-cyclohexenone) by proline-modified base-supported Pd catalysts is described. Effective combination of enhanced proline adsorption and secondary kinetic resolution resulted in very high enantioselectivities (ee up to 99\%). Using (S)- and (R)-proline enantiomers as chiral auxiliaries, both enantiomers of the product were obtained with excellent optical yields.",

keywords = "Chiral hydrogenation, Isophorone, Pd catalysts, Proline, Secondary kinetic resolution, Support effect",

author = "Mhadgut, \{Shilpa C.\} and Marianna T{\"o}r{\"o}k and Joseph Esquibel and B{\'e}la T{\"o}r{\"o}k",

year = "2006",

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doi = "10.1016/j.jcat.2006.01.004",

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journal = "Journal of Catalysis",

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T1 - Highly asymmetric heterogeneous catalytic hydrogenation of isophorone on proline modified base-supported palladium catalysts

AU - Mhadgut, Shilpa C.

AU - Török, Marianna

AU - Esquibel, Joseph

AU - Török, Béla

PY - 2006/3/10

Y1 - 2006/3/10

N2 - A highly effective asymmetric heterogeneous catalytic hydrogenation of isophorone (3,5,5-trimethyl-2-cyclohexenone) by proline-modified base-supported Pd catalysts is described. Effective combination of enhanced proline adsorption and secondary kinetic resolution resulted in very high enantioselectivities (ee up to 99%). Using (S)- and (R)-proline enantiomers as chiral auxiliaries, both enantiomers of the product were obtained with excellent optical yields.

AB - A highly effective asymmetric heterogeneous catalytic hydrogenation of isophorone (3,5,5-trimethyl-2-cyclohexenone) by proline-modified base-supported Pd catalysts is described. Effective combination of enhanced proline adsorption and secondary kinetic resolution resulted in very high enantioselectivities (ee up to 99%). Using (S)- and (R)-proline enantiomers as chiral auxiliaries, both enantiomers of the product were obtained with excellent optical yields.

KW - Chiral hydrogenation

KW - Isophorone

KW - Pd catalysts

KW - Proline

KW - Secondary kinetic resolution

KW - Support effect

UR - https://www.scopus.com/pages/publications/32344448336

UR - https://www.scopus.com/pages/publications/32344448336#tab=citedBy

U2 - 10.1016/j.jcat.2006.01.004

DO - 10.1016/j.jcat.2006.01.004

M3 - Article

AN - SCOPUS:32344448336

SN - 0021-9517

VL - 238

SP - 441

EP - 448

JO - Journal of Catalysis

JF - Journal of Catalysis

IS - 2

ER -

Highly asymmetric heterogeneous catalytic hydrogenation of isophorone on proline modified base-supported palladium catalysts

Abstract

ASJC Scopus Subject Areas

Keywords

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