A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives

Steven M. Allin; Christopher J. Northfield; Michael I. Page; Alexandra M Z Slawin

doi:10.1016/S0040-4039(97)00686-2

A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives

Steven M. Allin, Christopher J. Northfield, Michael I. Page, Alexandra M Z Slawin

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

54 Citations (Scopus)

Abstract

Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.

Original language	English
Pages (from-to)	3627-3630
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(97)00686-2
Publication status	Published - 19 May 1997

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10.1016/S0040-4039(97)00686-2

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title = "A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives",

abstract = "Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.",

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A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives. / Allin, Steven M.; Northfield, Christopher J.; Page, Michael I. et al.
In: Tetrahedron Letters, Vol. 38, No. 20, 19.05.1997, p. 3627-3630.

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

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T1 - A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives

AU - Allin, Steven M.

AU - Northfield, Christopher J.

AU - Page, Michael I.

AU - Slawin, Alexandra M Z

PY - 1997/5/19

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N2 - Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.

AB - Condensation of 2-formylbenzoic acid with α-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic γ-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives.

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DO - 10.1016/S0040-4039(97)00686-2

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A Highly Diastereoselective Synthesis of Tricyclic Lactams and their Application as Novel N-Acyl Iminium Ion Precursors in the Synthesis of Isoindolinone Derivatives

Abstract

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