Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine

Sally J. Oxenford, Stephen Moore, Giorgio Carbone, Graeme Barker, Peter O'Brien, Mark R. Shipton, John Gilday, Kevin R. Campos

Research output: Contribution to journal › Article

Abstract

The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (−)-swainsonine was completed.
Original languageEnglish
Pages (from-to)1563-1568
Number of pages6
JournalTetrahedron: Asymmetry
Volume21
Issue number11-12
DOIs
Publication statusPublished - 23 Jun 2010

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Swainsonine
Ions
Diamines
Alcohols

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Oxenford, Sally J. ; Moore, Stephen ; Carbone, Giorgio ; Barker, Graeme ; O'Brien, Peter ; Shipton, Mark R. ; Gilday, John ; Campos, Kevin R. / Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine. In: Tetrahedron: Asymmetry. 2010 ; Vol. 21, No. 11-12. pp. 1563-1568.
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abstract = "The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (−)-swainsonine was completed.",
author = "Oxenford, {Sally J.} and Stephen Moore and Giorgio Carbone and Graeme Barker and Peter O'Brien and Shipton, {Mark R.} and John Gilday and Campos, {Kevin R.}",
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Oxenford, SJ, Moore, S, Carbone, G, Barker, G, O'Brien, P, Shipton, MR, Gilday, J & Campos, KR 2010, 'Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine', Tetrahedron: Asymmetry, vol. 21, no. 11-12, pp. 1563-1568. https://doi.org/10.1016/j.tetasy.2010.03.048

Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine. / Oxenford, Sally J.; Moore, Stephen; Carbone, Giorgio; Barker, Graeme; O'Brien, Peter; Shipton, Mark R.; Gilday, John; Campos, Kevin R.

In: Tetrahedron: Asymmetry, Vol. 21, No. 11-12, 23.06.2010, p. 1563-1568.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine

AU - Oxenford, Sally J.

AU - Moore, Stephen

AU - Carbone, Giorgio

AU - Barker, Graeme

AU - O'Brien, Peter

AU - Shipton, Mark R.

AU - Gilday, John

AU - Campos, Kevin R.

PY - 2010/6/23

Y1 - 2010/6/23

N2 - The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (−)-swainsonine was completed.

AB - The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (−)-swainsonine was completed.

U2 - 10.1016/j.tetasy.2010.03.048

DO - 10.1016/j.tetasy.2010.03.048

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JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

SN - 0957-4166

IS - 11-12

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Oxenford SJ, Moore S, Carbone G, Barker G, O'Brien P, Shipton MR et al. Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine. Tetrahedron: Asymmetry. 2010 Jun 23;21(11-12):1563-1568. https://doi.org/10.1016/j.tetasy.2010.03.048

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