Synthesis of hydroxylated pyrrolidines by allenic cyclisation

Pearly Shuyi Ng; Roderick W. Bates

doi:10.1016/j.tet.2016.08.029

Synthesis of hydroxylated pyrrolidines by allenic cyclisation

Pearly Shuyi Ng, Roderick W. Bates^*

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

The diastereoselective gold(I) catalysed cyclisation of highly substituted aminoallene derivatives allows the synthesis of both epi-DAB-1 and di-epi-lentiginosine. While the sense of stereoselectivity observed is in line with earlier observations on analogous piperidine-forming cyclisations, different ligands and reaction conditions are required to obtain good yields.

Original language	English
Pages (from-to)	6356-6362
Number of pages	7
Journal	Tetrahedron
Volume	72
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2016.08.029
Publication status	Published - 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Alkaloid
Allene
Cyclisation
Diastereoselectivity
Gold

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10.1016/j.tet.2016.08.029

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abstract = "The diastereoselective gold(I) catalysed cyclisation of highly substituted aminoallene derivatives allows the synthesis of both epi-DAB-1 and di-epi-lentiginosine. While the sense of stereoselectivity observed is in line with earlier observations on analogous piperidine-forming cyclisations, different ligands and reaction conditions are required to obtain good yields.",

keywords = "Alkaloid, Allene, Cyclisation, Diastereoselectivity, Gold",

author = "Ng, {Pearly Shuyi} and Bates, {Roderick W.}",

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year = "2016",

doi = "10.1016/j.tet.2016.08.029",

language = "English",

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T1 - Synthesis of hydroxylated pyrrolidines by allenic cyclisation

AU - Ng, Pearly Shuyi

AU - Bates, Roderick W.

PY - 2016

Y1 - 2016

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AB - The diastereoselective gold(I) catalysed cyclisation of highly substituted aminoallene derivatives allows the synthesis of both epi-DAB-1 and di-epi-lentiginosine. While the sense of stereoselectivity observed is in line with earlier observations on analogous piperidine-forming cyclisations, different ligands and reaction conditions are required to obtain good yields.

KW - Alkaloid

KW - Allene

KW - Cyclisation

KW - Diastereoselectivity

KW - Gold

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U2 - 10.1016/j.tet.2016.08.029

DO - 10.1016/j.tet.2016.08.029

M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

Synthesis of hydroxylated pyrrolidines by allenic cyclisation

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

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