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Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates

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Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions : Comparison of (-)-sparteine and (+)-sparteine surrogates. / Canipa, Steven J.; Stute, Annika; O'Brien, Peter.

In: Tetrahedron, Vol. 70, No. 40, 10.2014, p. 7395-7403.

Research output: Contribution to journalArticle

Harvard

Canipa, SJ, Stute, A & O'Brien, P 2014, 'Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates', Tetrahedron, vol. 70, no. 40, pp. 7395-7403. https://doi.org/10.1016/j.tet.2014.06.117

APA

Canipa, S. J., Stute, A., & O'Brien, P. (2014). Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates. Tetrahedron, 70(40), 7395-7403. https://doi.org/10.1016/j.tet.2014.06.117

Vancouver

Canipa SJ, Stute A, O'Brien P. Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates. Tetrahedron. 2014 Oct;70(40):7395-7403. https://doi.org/10.1016/j.tet.2014.06.117

Author

Canipa, Steven J. ; Stute, Annika ; O'Brien, Peter. / Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions : Comparison of (-)-sparteine and (+)-sparteine surrogates. In: Tetrahedron. 2014 ; Vol. 70, No. 40. pp. 7395-7403.

Bibtex - Download

@article{f4a5ba6490e647ab80efc0fe235a9bf6,
title = "Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions: Comparison of (-)-sparteine and (+)-sparteine surrogates",
abstract = "Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexane-derived diamine were prepared and evaluated as chiral catalysts in desymmetrisation of . meso-diols and asymmetric Henry reactions. Mono-benzoylation reactions generated two products with high enantioselectivity (90:10 to 97:3 er). Asymmetric Henry reactions gave nitro alcohols in 90:10 to 98:2 er. Notably, the sense of induction with the (+)-sparteine surrogates was opposite to that obtained using the copper(II)/(-)-sparteine complex. One of the nitro alcohol products was utilised in a concise synthesis of a chiral morpholine.",
keywords = "Benzoylation, Copper(II) complexes, Diamines, Henry reaction, Morpholine",
author = "Canipa, {Steven J.} and Annika Stute and Peter O'Brien",
year = "2014",
month = "10",
doi = "10.1016/j.tet.2014.06.117",
language = "English",
volume = "70",
pages = "7395--7403",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "40",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Use of copper(II)/diamine catalysts in the desymmetrisation of meso-diols and asymmetric Henry reactions

T2 - Comparison of (-)-sparteine and (+)-sparteine surrogates

AU - Canipa, Steven J.

AU - Stute, Annika

AU - O'Brien, Peter

PY - 2014/10

Y1 - 2014/10

N2 - Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexane-derived diamine were prepared and evaluated as chiral catalysts in desymmetrisation of . meso-diols and asymmetric Henry reactions. Mono-benzoylation reactions generated two products with high enantioselectivity (90:10 to 97:3 er). Asymmetric Henry reactions gave nitro alcohols in 90:10 to 98:2 er. Notably, the sense of induction with the (+)-sparteine surrogates was opposite to that obtained using the copper(II)/(-)-sparteine complex. One of the nitro alcohol products was utilised in a concise synthesis of a chiral morpholine.

AB - Four new copper(II)/diamine complexes comprising some (+)-sparteine surrogates and a cyclohexane-derived diamine were prepared and evaluated as chiral catalysts in desymmetrisation of . meso-diols and asymmetric Henry reactions. Mono-benzoylation reactions generated two products with high enantioselectivity (90:10 to 97:3 er). Asymmetric Henry reactions gave nitro alcohols in 90:10 to 98:2 er. Notably, the sense of induction with the (+)-sparteine surrogates was opposite to that obtained using the copper(II)/(-)-sparteine complex. One of the nitro alcohol products was utilised in a concise synthesis of a chiral morpholine.

KW - Benzoylation

KW - Copper(II) complexes

KW - Diamines

KW - Henry reaction

KW - Morpholine

UR - http://www.scopus.com/inward/record.url?scp=84904437437&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.06.117

DO - 10.1016/j.tet.2014.06.117

M3 - Article

VL - 70

SP - 7395

EP - 7403

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 40

ER -