Stereoselective synthesis of new monoterpene β-amino alcohols

Łączkowski, Krzysztof Z.; Kmieciak, Anna; Kozakiewicz, Anna

doi:10.1016/j.tetasy.2009.06.007

Cited by 15 publications

(6 citation statements)

References 29 publications

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“…Specific rotation of these systems was previously calculated within the B3LYP/aVDZ approximation . We compare the B3LYP/ORP results with the available experimental data, and the aVDZ values.…”

Section: Introductionmentioning

confidence: 99%

The ORP basis set designed for optical rotation calculations

Baranowska-Łączkowska¹,

Łączkowski

2013

J. Comput. Chem.

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Details of generation of the optical rotation prediction (ORP) basis set developed for accurate optical rotation (OR) calculations are presented. Specific rotation calculations carried out at the density functional theory (DFT) level for model chiral methane molecule, fluorooxirane, methyloxirane, and dimethylmethylenecyclopropane reveal that the ORP set outperforms larger basis sets, among them the aug-cc-pVTZ basis set of Dunning (J. Chem. Phys. 1989, 90, 1007) and the aug-pc-2 basis set of Jensen (J. Chem. Phys. 2002, 117, 9234; J. Chem. Theory Comput. 2008, 4, 719). It is shown to be an attractive choice also in the case of larger systems, namely norbornanone, β-pinene, trans-pinane, and nopinone. The ORP basis set is further used in OR calculations for 24 other systems, and the results are compared to the aug-cc-pVDZ values. Whenever large discrepancies of results are observed, the ORP values are in an excellent agreement with the aug-cc-pVTZ results. The ORP basis set enables accurate specific rotation calculations at a reduced cost and thus can be recommended for routine DFT OR calculations, also for large and conformationally flexible molecules.

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Section: Introductionmentioning

confidence: 99%

The ORP basis set designed for optical rotation calculations

Baranowska-Łączkowska¹,

Łączkowski

2013

J. Comput. Chem.

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“…They constitute convenient starting materials for the synthesis of various 1,3-heterocycles for example (Ager et al 1996;Fülöp et al 1997;Gyonfalvi et al 2003;Kivelä et al 2003Kivelä et al , 2005. Although 1,2-amino alcohols have received much attention because they are generally readily accessible in enantiomerically pure form from natural precursors (Gyonfalvi et al 2003;Reetz et al 1987;Delair et al 1994;Masui and Shiori 1998;Laczkowski et al 2009;, the synthesis and the use of chiral 1,3-amino alcohols are still undergoing development and remain a challenge (Lait et al 2007;Didier et al 1991; Barluenga et al 1993; Bartoli et al 1994;Kossenjans and Martens 1999;Kochi et al 2003;Raghavan et al 2004;Murai et al 2005;Balazs et al 2007). …”

Section: Introductionmentioning

confidence: 99%

New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

et al. 2011

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“…In 2009, Łączkowski and co-workers described a convenient method for the stereoselective synthesis of b-amino alcohol 60 derived from (+)-3-carene. [56] The corresponding oxazaborolidine was prepared in situ by reaction of this b-amino alcohol with B(OiPr) 3 , then tested without isolation in the asymmetric reduction of prochiral ketones. Alcohols were obtained with excellent yields and enantioselectivities (Scheme 30).…”

Section: Oxazaborolidine Reductionsmentioning

confidence: 99%

Chiral Ligands Derived from Monoterpenes: Application in the Synthesis of Optically Pure Secondary Alcohols via Asymmetric Catalysis

Alami

Amrani

Agbossou‐Niedercorn

et al. 2014

Chemistry A European J

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The preparation of optically pure secondary alcohols in the presence of catalysts based on chiral ligands derived from monoterpenes, such as pinenes, limonenes and carenes, is reviewed. A wide variety of these ligands has been synthesized and used in several catalytic reactions, including hydrogen transfer, C-C bond formation via addition of organozinc compounds to aldehydes, hydrosilylation, and oxazaborolidine reduction, leading to high activities and enantioselectivities.

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Stereoselective synthesis of new monoterpene β-amino alcohols

Cited by 15 publications

References 29 publications

The ORP basis set designed for optical rotation calculations

The ORP basis set designed for optical rotation calculations

New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids

Chiral Ligands Derived from Monoterpenes: Application in the Synthesis of Optically Pure Secondary Alcohols via Asymmetric Catalysis

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