A novel stereoselective synthesis of N-heterocycles by intramolecular hydrovinylation

Ulrich Bothe; H. C. Rudbeck; David Ackland Tanner; Mogens Johannsen

doi:10.1039/b108310d

A novel stereoselective synthesis of N-heterocycles by intramolecular hydrovinylation

Ulrich Bothe, H. C. Rudbeck, David Ackland Tanner, Mogens Johannsen

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A novel method for the synthesis of bicyclic amines has been developed. Cyclisation of 1,6-dienes by intramolecular hydrovinylation in the presence of catalytic amounts of allylpalladium chloride dimer afforded bicyclic amines in one step. Added phosphines, silver salts, as well as the nature of the N-protecting group influenced the yield and selectivity of the reactions. Most strikingly, intramolecular hydrovinylation allowed the preparation of diastereomerically pure bicyclic amines as e.g. hexahydroindoles 2a-2d.

Original language	English
Journal	Royal Chemical Society. Journal. Perkin Transactions 1
Volume	1
Issue number	24
Pages (from-to)	3305-3311
ISSN	1472-7781
DOIs	https://doi.org/10.1039/b108310d
Publication status	Published - 2001

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10.1039/b108310d

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Bothe, U., Rudbeck, H. C., Tanner, D. A., & Johannsen, M. (2001). A novel stereoselective synthesis of N-heterocycles by intramolecular hydrovinylation. Royal Chemical Society. Journal. Perkin Transactions 1, 1(24), 3305-3311. https://doi.org/10.1039/b108310d

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abstract = "A novel method for the synthesis of bicyclic amines has been developed. Cyclisation of 1,6-dienes by intramolecular hydrovinylation in the presence of catalytic amounts of allylpalladium chloride dimer afforded bicyclic amines in one step. Added phosphines, silver salts, as well as the nature of the N-protecting group influenced the yield and selectivity of the reactions. Most strikingly, intramolecular hydrovinylation allowed the preparation of diastereomerically pure bicyclic amines as e.g. hexahydroindoles 2a-2d.",

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AU - Johannsen, Mogens

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N2 - A novel method for the synthesis of bicyclic amines has been developed. Cyclisation of 1,6-dienes by intramolecular hydrovinylation in the presence of catalytic amounts of allylpalladium chloride dimer afforded bicyclic amines in one step. Added phosphines, silver salts, as well as the nature of the N-protecting group influenced the yield and selectivity of the reactions. Most strikingly, intramolecular hydrovinylation allowed the preparation of diastereomerically pure bicyclic amines as e.g. hexahydroindoles 2a-2d.

AB - A novel method for the synthesis of bicyclic amines has been developed. Cyclisation of 1,6-dienes by intramolecular hydrovinylation in the presence of catalytic amounts of allylpalladium chloride dimer afforded bicyclic amines in one step. Added phosphines, silver salts, as well as the nature of the N-protecting group influenced the yield and selectivity of the reactions. Most strikingly, intramolecular hydrovinylation allowed the preparation of diastereomerically pure bicyclic amines as e.g. hexahydroindoles 2a-2d.

U2 - 10.1039/b108310d

DO - 10.1039/b108310d

M3 - Journal article

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JF - Royal Chemical Society. Journal. Perkin Transactions 1

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