A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols

Arunkumar Natarajan; V. Ramamurthy; Joel T. Mague

doi:10.1080/15421400600786355

A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols

Arunkumar Natarajan, V. Ramamurthy, Joel T. Mague

Chemistry

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

4 Scopus citations

Abstract

The effectiveness of chiral auxiliaries in inducing diastereoselectivity during photocyclization of ten differnt α-mesitylacetophenones to 2-indanols in crystalline state and as zeolite inclusion complexes has been examined. In the systems examined the chiral auxiliary functioned better within zeolites than in crystals. Crystal structure analysis of three α-mesitylacetophenones revealed that the low chiral induction in the crystalline state is either due to the presence of conformational isomerism in the reactant part of the molecule or the absence of communication between the chiral auxiliary and the reactant part of the ketone.

Original language	English (US)
Pages (from-to)	71-84
Number of pages	14
Journal	Molecular crystals and liquid crystals
Volume	456
Issue number	1
DOIs	https://doi.org/10.1080/15421400600786355
State	Published - Oct 1 2006

Keywords

δ-hydrogen abstraction
Chiral induction
Crystalline state
Diastereoselectivity
Mesitylacetophenones
Photocyclization
Zeolites

ASJC Scopus subject areas

Condensed Matter Physics

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10.1080/15421400600786355

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title = "A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols",

abstract = "The effectiveness of chiral auxiliaries in inducing diastereoselectivity during photocyclization of ten differnt α-mesitylacetophenones to 2-indanols in crystalline state and as zeolite inclusion complexes has been examined. In the systems examined the chiral auxiliary functioned better within zeolites than in crystals. Crystal structure analysis of three α-mesitylacetophenones revealed that the low chiral induction in the crystalline state is either due to the presence of conformational isomerism in the reactant part of the molecule or the absence of communication between the chiral auxiliary and the reactant part of the ketone.",

keywords = "δ-hydrogen abstraction, Chiral induction, Crystalline state, Diastereoselectivity, Mesitylacetophenones, Photocyclization, Zeolites",

author = "Arunkumar Natarajan and V. Ramamurthy and Mague, {Joel T.}",

note = "Funding Information: V. R. thanks the NSF (CHE-0212042) for financial support and JTM thanks the Louisiana Board of regents through the Louisiana Educational Quality Support Fund [Grant No. LEQSF (2003-2003)-ENH-TR-67] for the purchase of the Bruker APEX diffractometer.",

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T2 - Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols

AU - Natarajan, Arunkumar

AU - Ramamurthy, V.

AU - Mague, Joel T.

N1 - Funding Information: V. R. thanks the NSF (CHE-0212042) for financial support and JTM thanks the Louisiana Board of regents through the Louisiana Educational Quality Support Fund [Grant No. LEQSF (2003-2003)-ENH-TR-67] for the purchase of the Bruker APEX diffractometer.

PY - 2006/10/1

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N2 - The effectiveness of chiral auxiliaries in inducing diastereoselectivity during photocyclization of ten differnt α-mesitylacetophenones to 2-indanols in crystalline state and as zeolite inclusion complexes has been examined. In the systems examined the chiral auxiliary functioned better within zeolites than in crystals. Crystal structure analysis of three α-mesitylacetophenones revealed that the low chiral induction in the crystalline state is either due to the presence of conformational isomerism in the reactant part of the molecule or the absence of communication between the chiral auxiliary and the reactant part of the ketone.

AB - The effectiveness of chiral auxiliaries in inducing diastereoselectivity during photocyclization of ten differnt α-mesitylacetophenones to 2-indanols in crystalline state and as zeolite inclusion complexes has been examined. In the systems examined the chiral auxiliary functioned better within zeolites than in crystals. Crystal structure analysis of three α-mesitylacetophenones revealed that the low chiral induction in the crystalline state is either due to the presence of conformational isomerism in the reactant part of the molecule or the absence of communication between the chiral auxiliary and the reactant part of the ketone.

KW - δ-hydrogen abstraction

KW - Chiral induction

KW - Crystalline state

KW - Diastereoselectivity

KW - Mesitylacetophenones

KW - Photocyclization

KW - Zeolites

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